Boron tribromide → 4-(4-Hydroxybutyl)phenol

HRID 511989Notes

Reaction equation

HRID 511989 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][OH:13])=[CH:5][CH:4]=1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][OH:13])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromide3×HCID 976604-(4-Methoxyphenyl)butan-1-ol

Product 1

HCID 133925134-(4-Hydroxybutyl)phenolYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 4-(4-methoxyphenyl)butanol (1 equiv.) in dry dichloromethane at −10° C. under an argon atmosphere was added boron tribromide (2.7 equiv., using a 1 M solution of boron tribromide in CH2Cl2). Stirring was continued at that temperature until completion of the reaction (4 hours). Unreacted boron tribromide was destroyed by addition of aqueous saturated NaHCO3 solution at 0° C. The resulting mixture diluted with CH2Cl2 and water, the organic phase was separated, washed with brine, dried (MgSO4) and evaporated. Purification by flash column chromatography on silica gel (30% diethyl ether-hexane) afforded the title compound in 42% yield.

Workup

  1. customwas continued at that temperature until completion of the reaction (4 hours)
  2. customwas destroyed by addition of aqueous saturated NaHCO3 solution at 0° C
  3. additionThe resulting mixture diluted with CH2Cl2 and water
  4. customthe organic phase was separated
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customPurification by flash column chromatography on silica gel (30% diethyl ether-hexane)

Sources & evidence

ORD record
ord-9972794c6f1e4224987c7213f2d89f42
Source dataset
uspto-grants-2015_08
Patent number
US09102622B2

Reaction notes

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