1,4-Dibromobenzene → Benzenemethanol, 4-bromo-alpha-ethyl-alpha-(trifluoromethyl)-

HRID 2217284Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.[Li]CCCC.[F:14][C:15]([F:21])([F:20])[C:16](=[O:19])[CH2:17][CH3:18]>C1COCC1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:16]([OH:19])([CH2:17][CH3:18])[C:15]([F:21])([F:20])[F:14])=[CH:3][CH:4]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 1,4-dibromobenzene (2.5 g, 10.6 mmol) in THF (50 mL) at −78° C. was added n-BuLi (6.5 mL, 10 mmol; 1.6 M in hexanes) and the mixture was stirred at −78° C. for 15 min. 1,1,1-Trifluoro-2-butanone (1.3 g, 10 mmol) was then added. After further stirring for 15 min., the mixture was quenched with aqueous NH4Cl and extracted with Ethyl acetate. Purification by combi-flash chromatography (40 g column; eluted with hexanes—Ethyl acetate (10% -20%) in 20 min.; flow rate: 35 mL/min and collected 18 mL/fraction) to yield the title compound as a colorless liquid.

Workup

stirringAfter further stirring for 15 min.
customthe mixture was quenched with aqueous NH4Cl
extractionextracted with Ethyl acetate
customPurification
washby combi-flash chromatography (40 g column; eluted with hexanes—Ethyl acetate (10% -20%) in 20 min.; flow rate: 35 mL/min and collected 18 mL/fraction)

Sources & evidence

ORD record: ord-410d80df641e4d1caa592e182a093078
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07407959B2

Reaction notes

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