Hydrochloric Acid → 4-((5-Bromo-2-chlorophenyl)methyl)phenol

HRID 19823Notes

Reaction equation

HRID 19823 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16]C)=[CH:12][CH:11]=2)[CH:3]=1.B(Br)(Br)Br.C(=O)([O-])[O-].[K+].[K+].Cl>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([CH:3]=1)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 25134Boron tribromideHCID 223285944-Bromo-1-chloro-2-(4-methoxybenzyl)benzene

Product 1

HCID 574237514-((5-Bromo-2-chlorophenyl)methyl)phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 14.8 g 1-bromo-4-chloro-3-(4-methoxy-benzyl)-benzene in 150 mL dichloromethane is cooled in an ice bath. 50 mL of a 1 M solution of boron tribromide in dichloromethane are added and the resulting solution is stirred for 2 h at ambient temperature. The solution is then cooled in an ice bath again and saturated aqueous potassium carbonate solution is added dropwise. At ambient temperature the mixture is adjusted with aqueous 1 M hydrochloric acid to pH 1, the organic phase is separated off and the aqueous phase is extracted three times with ethyl acetate. The combined organic phases are dried over sodium sulfate and the solvent is removed completely.

Workup

  1. temperatureThe solution is then cooled in an ice bath again
  2. customAt ambient temperature
  3. customthe organic phase is separated off
  4. extractionthe aqueous phase is extracted three times with ethyl acetate
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. customthe solvent is removed completely

Sources & evidence

ORD record
ord-1478545e3d4e4e06bc3aedf1e64970b7
Source dataset
uspto-grants-2010_06
Patent number
US07745414B2

Reaction notes

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