Sulfuric Acid → HCID 12423586, compound

HRID 839693Notes

Reaction equation

HRID 839693 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:21])[C:12]([C:14]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=1)=[CH2:13].S(=O)(=O)(O)O>ClCCl>[Br:20][C:17]1[CH:16]=[CH:15][C:14]([CH:12]2[CH2:13][C:4]3[C:3](=[C:2]([Cl:1])[C:7]([Cl:8])=[C:6]([O:9][CH3:10])[CH:5]=3)[C:11]2=[O:21])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 12282424HCID 12282424, compound

Product 1

HCID 12423586HCID 12423586, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2',3'-Dichloro-4'-methoxy-2-(4-bromophenyl)acrylophenone (143 g., 0.37 mole) dissolved in dichloromethane (2 l.) is drizzled into cold 36N sulfuric acid (1 l.)-dichloromethane (1 l.) in an ice bath over 4 hours. After stirring for an additional half hour, the reaction mixture is slowly added to crushed ice, the dichloromethane layer separated, washed with saturated salt solution, concentrated in vacuo to give 134.8 g. of 2-(4-bromophenyl)-5-methoxy-6,7-dichloro-1-indanone which melts at 202°-203° C. after trituration with water followed by crystallization from benzene:hexane, 1:1.

Workup

  1. additionthe reaction mixture is slowly added
  2. customto crushed ice
  3. customthe dichloromethane layer separated
  4. washwashed with saturated salt solution
  5. concentrationconcentrated in vacuo
  6. customto give 134.8 g
  7. customof 2-(4-bromophenyl)-5-methoxy-6,7-dichloro-1-indanone which melts at 202°-203° C. after trituration with water followed by crystallization from benzene

Sources & evidence

ORD record
ord-29ec3828209c4b94acf34911856c4225
Source dataset
uspto-grants-1978_06
Patent number
US04096267

Reaction notes

Loading…