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

HRID 746809Notes

Reaction equation

HRID 746809 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 the 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 again in the ice bath, and saturated potassium carbonate solution is added dropwise. At ambient temperature the mixture is adjusted to a pH of 1 with aqueous 1 M hydrochloric acid, the organic phase is separated off and the aqueous phase is extracted another three times with ethyl acetate. The combined organic phases are dried over sodium sulphate, and the solvent is totally eliminated.

Workup

  1. additionis added dropwise
  2. customAt ambient temperature
  3. customthe organic phase is separated off
  4. extractionthe aqueous phase is extracted another three times with ethyl acetate
  5. dry with materialThe combined organic phases are dried over sodium sulphate

Sources & evidence

ORD record
ord-4d04b2412116459f88afcfe07e7bdf7d
Source dataset
uspto-grants-2008_07
Patent number
US07393836B2

Reaction notes

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