Acetone → 2-(5-Bromopyridin-2-yl)propan-2-ol

HRID 1839149Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.C([Li])CCC.[CH3:14][C:15]([CH3:17])=[O:16]>C1(C)C=CC=CC=1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:15]([OH:16])([CH3:17])[CH3:14])=[N:3][CH:4]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a suspension of 2,5-dibromopyridine in toluene (12 ml/mmol) cooled to −78° C. was added n-butyllithium 2.5M in hexanes (1.05 eq) and the resulting mixture was stirred in the cold for 2.5 hours. Acetone (2 eq) was added and stirring was continued for 1.5 h. After quenching with saturated aqueous ammonium chloride solution, the mixture was warmed to room temperature and partitioned between ethyl acetate and water. The product from the organic phase was chromatographed on silica gel eluting with 20% ethyl acetate in hexane to afford the 5-Bromo-2-(1-hydroxy-1-methylethyl) pyridine compound as a syrup.

Workup

stirringstirring
waitwas continued for 1.5 h
customAfter quenching with saturated aqueous ammonium chloride solution
temperaturethe mixture was warmed to room temperature
custompartitioned between ethyl acetate and water
customThe product from the organic phase was chromatographed on silica gel eluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record: ord-e067bef201b24df89e9f5fd63ac11a09
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06677351B2

Reaction notes

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