Lithium borohydride → 2,3-Difluoro-5-methoxybenzenemethanol

To a solution of 2,3-difluoro-5-methoxy-benzoic acid methyl ester (925 mg, 4.58 mmol) in THF (25 mL), cooled to 0° C., was added a solution of LiBH4 (199 mg, 9.15 mmol) in THF (5 mL). The reaction mixture was stirred at RT for overnight. An additional aliquot of LiBH4 (4 equiv) was added and stirring was continued at RT for 6 h, and subsequently at 60° C. overnight. The mixture was diluted with EtOAc, the organics were washed with 1N aqueous NaOH solution (50 mL), dried (Phase separator) and evaporated in vacuo to afford the title compound as a white solid. TLC Rf (c-hexane/EtOAc 1:1)=0.57; MS (LC/MS): 198.0 [M+Na]+; tR (HPLC conditions c): 3.74 min.

1. stirringstirring
2. waitwas continued at RT for 6 h
3. customsubsequently at 60° C.
4. customovernight
5. washthe organics were washed with 1N aqueous NaOH solution (50 mL)
6. customdried (Phase separator)
7. customevaporated in vacuo

ORD record

ord-7d0d86f219304db09219a9785990f41c

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09085555B2