| Identification | Back Directory | [Name]
TERT-BUTYL-4-BROMOBENZOATE | [CAS]
59247-47-1 | [Synonyms]
TERT-BUTYL-4-BROMOBENZOATE
tert-Butyl p-BroMobenzoate
4-Bromobenzoic acid tert-butyl ester
4-BroMobenzoic Acid 1,1-DiMethylethyl Ester
Benzoic acid, 4-broMo-, 1,1-diMethylethyl ester | [Molecular Formula]
C11H13BrO2 | [MDL Number]
MFCD00093266 | [MOL File]
59247-47-1.mol | [Molecular Weight]
257.12 |
| Chemical Properties | Back Directory | [Boiling point ]
91-92 °C(Press: 1.2 Torr) | [density ]
1.331±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
liquid | [color ]
Colourless to light yellow | [InChI]
InChI=1S/C11H13BrO2/c1-11(2,3)14-10(13)8-4-6-9(12)7-5-8/h4-7H,1-3H3 | [InChIKey]
BFJJYXUCGYOXDM-UHFFFAOYSA-N | [SMILES]
C(OC(C)(C)C)(=O)C1=CC=C(Br)C=C1 |
| Hazard Information | Back Directory | [Uses]
4-bromo substituted benzoic acid derivative, tert-Butyl-4-broMobenzoate can be used as a building block for the synthesis of various biologically active compounds.
| [Synthesis]
At -78 °C, 4-bromobenzoyl chloride (25.08 g, 114 mmol) was dissolved in THF (120 mL) and a THF solution of potassium tert-butanolate (1 M, 120 mL, 120 mmol) was slowly added. The reaction mixture was stirred at -78 °C and gradually warmed to room temperature for 2 hours. After completion of the reaction, the reaction mixture was diluted with ether. The organic phase was washed sequentially with saturated NaHCO3 solution (2×) and brine (1×) and then dried with anhydrous MgSO4. The desiccant was removed by filtration and the filtrate was concentrated under reduced pressure. The crude product was purified by fast column chromatography on silica gel, the eluent being a hexane solution of 5% ethyl acetate to give tert-butyl 4-bromobenzoate (27.96 g, 95% yield) as a colorless oil.1H NMR (600 MHz, CDCl3) δ 7.84 (d, J = 8.5 Hz, 2H), 7.54 (d, J = 8.5 Hz, 2H), 1.59 (s 9H); ESIMS calculated value 257.0 (M + + H), measured value 257.1 (M + + H). | [References]
[1] RSC Advances, 2016, vol. 6, # 22, p. 18165 - 18177
[2] Journal of Organic Chemistry, 2000, vol. 65, # 17, p. 5428 - 5430
[3] Patent: WO2007/2248, 2007, A2. Location in patent: Page/Page column 72-73
[4] Organic Process Research and Development, 2012, vol. 16, # 11, p. 1832 - 1845
[5] Journal of the American Chemical Society, 2016, vol. 138, # 32, p. 10293 - 10298 |
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