1,4-Dibromobenzene → 2-(4-Bromophenyl)-1,1,1-trifluoropropan-2-ol

Temperature

-78 °C

A 500 mL round-bottomed flask was charged with 1,4-dibromobenzene (30.27 g, 128 mmol, Sigma-Aldrich, St. Louis, Mo.) and 200 mL of ether. After cooling to −78° C., n-BuLi (59.0 mL, 2.5 M in hexanes, 148 mmol) was added. This mixture was stirred for 15 min at −78° C., then 1,1,1-trifluoro-2-propanone (24.2 mL, 257 mmol, Sigma-Aldrich, St. Louis, Mo.) was added. Stirring was continued at −78° C. for 30 min then the mixture was quenched with 100 mL of saturated aqueous NH4Cl. The mixture was extracted with EtOAc (250 mL), dried (MgSO4) and concentrated to give an oil. Purification via column chromatography (330 g of silica, 0 to 30% EtOAc in hexanes) gave 2-(4-bromophenyl)-1,1,1-trifluoro-2-propanol (21.50 g) as a colorless oil.

1. stirringStirring
2. waitwas continued at −78° C. for 30 min
3. customthe mixture was quenched with 100 mL of saturated aqueous NH4Cl
4. extractionThe mixture was extracted with EtOAc (250 mL)
5. dry with materialdried (MgSO4)
6. concentrationconcentrated
7. customto give an oil
8. customPurification via column chromatography (330 g of silica, 0 to 30% EtOAc in hexanes)

ORD record

ord-9d7ac375ca6d4a9289123868e2c53116

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08431563B2