[Li]CCCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:8]=1[CH:14]([OH:17])[CH2:15][CH3:16].[B:18](OC(C)C)([O:23]C(C)C)[O:19]C(C)C.Cl>CCCCC.C1COCC1>[F:13][C:9]1[C:8]([CH:14]([OH:17])[CH2:15][CH3:16])=[C:7]([B:18]([OH:23])[OH:19])[CH:12]=[CH:11][CH:10]=1A solution of n-BuLi (2.15 mL, 4.3 mmol) in pentane (2 M) is added dropwise to a solution of 1-(2-bromo-6-fluoro-phenyl)-propan-1-ol (500 mg, 2.15 mmol) in THF at −78° C. The mixture is stirred for 2 hours at −78° C. (i-PrO)3B (41 mL, 4.3 mmol) is added in one portion and the mixture is warmed slowly to room temperature and stirred for 12 hours. 1N HCl (10 mL) is added and the mixture is stirred for 2 hours at room temperature. The organic layer is separated and the aqueous layer is extracted with DCM (3×30 mL). The combined organic layers are dried and solvents are removed in vacuo. The crude product is purified by PTLC eluting with 5% MeOH in DCM to give 3-fluoro-2-(1-hydroxypropyl)phenylboronic acid.
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