2,3-Dichloroanisole → HCID 12423580, compound

HRID 839692Notes

Reaction equation

HRID 839692 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9][CH3:10].[Br:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19](Cl)=[O:20])=[CH:14][CH:13]=1.[Cl-].[Al+3].[Cl-].[Cl-]>C(=S)=S>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:19](=[O:20])[CH2:18][C:15]2[CH:16]=[CH:17][C:12]([Br:11])=[CH:13][CH:14]=2)[CH:5]=[CH:4][C:3]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 161262,3-DichloroanisoleHCID 181552Benzeneacetyl chloride, 4-bromo-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 12423580HCID 12423580, compound

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a stirred mixture of 2,3-dichloroanisole (73.5 g., 0.414 mole), 4-bromophenylacetyl chloride (105 g., 0.456 mole) and carbon disulfide (300 ml.) is added portionwise aluminum chloride (60.9 g., 0.456 mole) with cooling at 0°-5° C. The reaction mixture is left at 25° C. for 17 hours, then flushed with nitrogen, and the solid residue treated with crushed ice and 12N hydrochloric acid (80 ml.) to give 147.7 g. of 2,3-dichloro-4-(4-bromophenyl)acetylanisole which melts at 163°-164.5° C. after crystallization from benzene:hexane, 1:1.

Workup

  1. temperaturewith cooling at 0°-5° C
  2. customflushed with nitrogen
  3. additionthe solid residue treated with crushed ice and 12N hydrochloric acid (80 ml.)
  4. customto give 147.7 g
  5. customof 2,3-dichloro-4-(4-bromophenyl)acetylanisole which melts at 163°-164.5° C. after crystallization from benzene

Sources & evidence

ORD record
ord-6f305a936b754a38b9db06304915a2e5
Source dataset
uspto-grants-1978_06
Patent number
US04096267

Reaction notes

Loading…