Butyl bromide → HCID 19010753, compound

HRID 1741842Notes

Reaction equation

HRID 1741842 reaction equation
[Mg:1].Br[CH2:3][CH2:4][CH2:5][CH3:6].[Br:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[C:10]([F:16])[CH:9]=1>C(OCC)C>[CH2:3]([Mg:1][Br:7])[CH2:4][CH2:5][CH3:6].[Br:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]([OH:13])[CH2:3][CH2:4][CH2:5][CH3:6])=[C:10]([F:16])[CH:9]=1

Participants

6

Reactant 3

HCID 8002Butyl bromideHCID 1435174-Bromo-2-fluorobenzaldehydeHCID 5462224Magnesium

Product 2

HCID 19010753HCID 19010753, compoundYield 106.8%HCID 178418682HCID 178418682, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of butylmagnesium bromide was prepared in the usual manner with diethyl ether (5 ml), magnesium (111 mg) and 1-bromobutane (624 mg). A solution of 4-bromo-2-fluorobenzaldehyde (925 mg) in diethyl ether (5 ml) was added dropwise to the Grignard solution. After the addition was completed, the reaction mixture was stirred for 30 minutes at room temperature. The reaction was quenched with aqueous ammonium chloride and the organic layer was separated, washed with water and brine, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel column eluting with a mixture of hexane and ethyl acetate (85:15) to give 1-(4-bromo-2-fluorophenyl)pentanol (635 mg) as an oil.

Workup

  1. additionAfter the addition
  2. customThe reaction was quenched with aqueous ammonium chloride
  3. customthe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel column
  8. washeluting with a mixture of hexane and ethyl acetate (85:15)

Sources & evidence

ORD record
ord-d01e7184a51243aebc53d9497c181bab
Source dataset
uspto-grants-1994_08
Patent number
US05334716

Reaction notes

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