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

HRID 2245909Notes

Reaction equation

HRID 2245909 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 4-bromo-1-chloro-2-(4-methoxy-benzyl)-benzene in 150 mL dichloromethane is cooled in an ice bath. Then 50 mL of a 1 M solution of boron tribromide in dichloromethane are added, and the solution is stirred for 2 h at ambient temperature. The solution is then cooled in an ice bath again, and saturated potassium carbonate solution is added dropwise. At ambient temperature the mixture is adjusted with aqueous 1 M hydrochloric acid to a pH of 1, the organic phase is separated and the aqueous phase is extracted another 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
  4. extractionthe aqueous phase is extracted another 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-06572c9d48a44bcba052696c09740491
Source dataset
uspto-grants-2010_03
Patent number
US07683160B2

Reaction notes

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