Sulfuric Acid → HCID 12423586, compound

HRID 2052047Notes

Reaction equation

HRID 2052047 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 36 N 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-4497f7583d0e49a5aeca6b355c124e7b
Source dataset
uspto-grants-1980_01
Patent number
US04182764

Reaction notes

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