Acetic Anhydride → HCID 12282424, compound

HRID 2052046Notes

Reaction equation

HRID 2052046 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9](=[O:18])[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=2)[CH:5]=[CH:4][C:3]=1[O:19][CH3:20].[C:21](OC(=O)C)(=O)C>CN(CN(C)C)C>[Cl:8][C:7]1[C:2]([Cl:1])=[C:3]([O:19][CH3:20])[CH:4]=[CH:5][C:6]=1[C:9](=[O:18])[C:10]([C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=1)=[CH2:21]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 12423580HCID 12423580, compound

Product 1

HCID 12282424HCID 12282424, compound

Reagents, catalysts & solvents 1

HCID 5829N,N,N',N'-TetramethylmethanediamineSolvent

Conditions

Temperature
25 °C

Procedure

To a suspension of 2,3-dichloro-4-(4-bromophenyl)acetyl anisole (142.5 g., 0.38 mole) in bis-dimethylaminomethane (325 ml.) under nitrogen is added dropwise acetic anhydride (325 ml.) with cooling to maintain the reaction mixture temperature below 40° C. The reaction mixture is stirred at 25° C. for one hour, then poured into crushed ice-water (4 l.) to precipitate 143 g. of 2',3'-dichloro-4'-methoxy-2-(4-bromophenyl)acrylophenone which melts at 110°-116° C. after crystallization from benzene:hexane, 1:5.

Workup

  1. temperaturewith cooling
  2. temperatureto maintain the reaction mixture temperature below 40° C
  3. additionpoured
  4. customto precipitate 143 g
  5. customof 2',3'-dichloro-4'-methoxy-2-(4-bromophenyl)acrylophenone which melts at 110°-116° C. after crystallization from benzene

Sources & evidence

ORD record
ord-0696dc3c45ce4264ae3ede07436dcbc9
Source dataset
uspto-grants-1980_01
Patent number
US04182764

Reaction notes

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