2-Acetyl-5-bromothiophene → 5-Bromo-alpha,alpha-dimethyl-2-thiophenemethanol

HRID 351749

Reaction equation

[C:1]([C:4]1[S:5][C:6]([Br:9])=[CH:7][CH:8]=1)(=[O:3])[CH3:2].[CH3:10][Mg]Br.C1(C)C=CC=CC=1.C1COCC1>C1COCC1>[Br:9][C:6]1[S:5][C:4]([C:1]([OH:3])([CH3:10])[CH3:2])=[CH:8][CH:7]=1

Participants

Conditions

Temperature: -10 °C

Procedure

To a solution of 2-acetyl-5-bromothiophene in THF (2.5 mL/mmol) at −30° C. was added 1.4M methylmagnesium bromide in 3:1 toluene-THF (1.5 eq) and the resulting mixture was warmed to −10° C. and stirred for 1.5 hours. After quenching with saturated aqueous ammonium chloride solution, the mixture was partitioned between ether and water. The organic fraction was dried and evaporated, and the crude material was chromatographed on silica gel eluting with a 1:4 mixture of ether and hexane to afford the 2-bromo-5-(1-hydroxy-1-methylethyl)thiophene compound.

Workup

customAfter quenching with saturated aqueous ammonium chloride solution
customthe mixture was partitioned between ether and water
customThe organic fraction was dried
customevaporated
customthe crude material was chromatographed on silica gel eluting with a 1:4 mixture of ether and hexane

Sources & evidence

ORD record: ord-1e0a865ae353492d95932dc9687937af
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06743802B2

Linked notes

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