Bromine → 2-Bromo-2',3'-dichloro-4'-methoxyisobutyrophenone

HRID 597000Notes

Reaction equation

HRID 597000 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([O:9][CH3:10])[CH:5]=[CH:4][C:3]=1[C:11](=[O:15])[CH:12]([CH3:14])[CH3:13].[Br:16]Br.S(=O)(O)[O-].[Na+]>C(O)(=O)C>[Br:16][C:12]([CH3:13])([CH3:14])[C:11]([C:3]1[CH:4]=[CH:5][C:6]([O:9][CH3:10])=[C:7]([Cl:8])[C:2]=1[Cl:1])=[O:15]

Participants

5

Reactant 3

HCID 24408BromineHCID 123955502',3'-Dichloro-4'-methoxyisobutyrophenoneHCID 23665763Sodium Bisulfite

Product 1

HCID 123956042-Bromo-2',3'-dichloro-4'-methoxyisobutyrophenone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred solution of 2',3'-dichloro-4'methoxyisobutyrophenone (45 g., 0.183 mole) in acetic acid (150 ml.) is treated during 1/2 hour with bromine (30 g., 0.187 mole). The reaction mixture is stirred 10 minutes, then poured into ice water (600 ml.) containing sodium bisulfite (2 g.). The 2-bromo-2'-3'-dichloro-4'-methoxyisobutyrophenone which separates (48 g.) melts at 72°-73° C. after recrystallization from hexane.

Workup

  1. customafter recrystallization from hexane

Sources & evidence

ORD record
ord-12e688d281ce4f70a40f06af7c32c271
Source dataset
uspto-grants-1977_03
Patent number
US04012524

Reaction notes

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