Benzene → HCID 12423595, compound

HRID 1447690Notes

Reaction equation

HRID 1447690 reaction equation
C[O-].[Na+].[Br:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:19][C:18]3[C:13](=[C:14]([Cl:23])[C:15]([Cl:22])=[C:16]([O:20][CH3:21])[CH:17]=3)[C:12]2=[O:24])=[CH:7][CH:6]=1.IC.[CH:27]1C=CC=CC=1>O.CN(C)C=O>[Br:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2([CH3:27])[CH2:19][C:18]3[C:13](=[C:14]([Cl:23])[C:15]([Cl:22])=[C:16]([O:20][CH3:21])[CH:17]=3)[C:12]2=[O:24])=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 241BenzeneHCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 12423586HCID 12423586, compound

Product 1

HCID 12423595HCID 12423595, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium methoxide (28.4 g., 0.522 mole) is added to a stirred mixture of 2-(4-bromophenyl)-5-methoxy-6,7-dichloro-1-indanone (134.6 g., 0.348 mole), iodomethane (217 ml., 3.48 mole), dry benzene (1700 ml.) and dry dimethylformamide (1700 ml.) under nitrogen in an ice-water bath. The reaction mixture is left to come to ambient temperature over 2 hours, then poured into water (8 l.) to precipitate 92.2 g. of 2-(4-bromophenyl)-2-methyl-5-methoxy-6,7-dichloro-1-indanone, m.p. 200°-203° C., which is not soluble in the benzene present.

Workup

  1. waitThe reaction mixture is left
  2. customto precipitate 92.2 g

Sources & evidence

ORD record
ord-16e69d2043e44134bc7620212e3afac5
Source dataset
uspto-grants-1979_12
Patent number
US04177285

Reaction notes

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