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

HRID 1484884Notes

Reaction equation

HRID 1484884 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7](=[O:9])[CH3:8])=[CH:4][CH:3]=1.[CH3:10][Mg]Br>CCOCC>[Br:1][C:2]1[S:6][C:5]([C:7]([OH:9])([CH3:10])[CH3:8])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 793352-Acetyl-5-bromothiopheneHCID 178418573HCID 178418573, compound

Product 1

HCID 227143025-Bromo-alpha,alpha-dimethyl-2-thiophenemethanolYield 89.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To the solution of 1-(5-bromothiophen-2-yl)ethanone (2.05 g, 10 mmol, 1 eq) in ether (20 mL) was added methylmagnesium bromide (11 mL, 11 mmol, 1.1 eq) dropwise at ice-bath. After 0.5 h, the reaction mixture was allowed to stand at room temperature for 1.5 h. Then, the reaction was quenched with saturated aqueous NH4Cl, washed with brine, dried (Na2SO4), and evaporated to afford 2-(5-bromothiophen-2-yl)propan-2-ol (1.97 g, 89%). LC-MS (m/z)=211 [M+]H+.

Workup

  1. waitto stand at room temperature for 1.5 h
  2. customThen, the reaction was quenched with saturated aqueous NH4Cl
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-d700dd36c03f429a83033e0602d19d26
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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