2-Bromobenzaldehyde → 1-(2-Bromophenyl)-1-propanol

HRID 993324Notes

Reaction equation

HRID 993324 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:10]([Mg]Br)[CH3:11]>C1COCC1>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]([OH:5])[CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 811292-BromobenzaldehydeHCID 178418443HCID 178418443, compound

Product 1

HCID 134442791-(2-Bromophenyl)-1-propanolYield 102.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-bromobenzaldehyde (1.85 g, 10 mmol) in THF (30 mL) at −70° C. was treated with 3 M solution of ethylmagnesium bromide (3.5 mL, 10.5 mmol). The mixture was warmed to room temperature for 6 hours and quenched with saturated solution of NH4Cl. The mixture was extracted with ethyl ether to provide the crude alcohol (yield: 2.2 g; ˜100%).

Workup

  1. customquenched with saturated solution of NH4Cl
  2. extractionThe mixture was extracted with ethyl ether

Sources & evidence

ORD record
ord-cabfe51b5f1c44e6bf266c751376711f
Source dataset
uspto-grants-2002_10
Patent number
US06472416B1

Reaction notes

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