Hydrochloric Acid → HCID 12423611, compound

HRID 1447691Notes

Reaction equation

HRID 1447691 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:21])[CH2:16][C:15]3[C:10](=[C:11]([Cl:19])[C:12]([Cl:18])=[C:13]([OH:17])[CH:14]=3)[C:9]2=[O:20])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][C:30]([O:32]CC)=[O:31].[OH-].[Na+].Cl>CN(C)C=O.O>[O:20]=[C:9]1[C:10]2[C:15](=[CH:14][C:13]([O:17][CH2:29][C:30]([OH:32])=[O:31])=[C:12]([Cl:18])[C:11]=2[Cl:19])[CH2:16][C:8]1([C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)[CH3:21]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 12423603HCID 12423603, compound

Product 1

HCID 12423611HCID 12423611, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A stirred mixture of 2-(4-bromophenyl)-2-methyl-5-hydroxy-6,7-dichloro-1-indanone (4.48 g., 0.0116 mole), potassium carbonate (3.88 g., 0.0232 mole) and ethyl bromoacetate (3.21 g., 0.0232 mole) in dimethylformamide (100 ml.) is warmed at 55°-60° C. for 3 hours, then treated with water (100 ml.)-10 N sodium hydroxide solution (5 ml., 0.05 mole) and heated at 100° C. for 2 hours. The reaction mixture is added slowly to crushed ice-water (1500 ml.)-12 N hydrochloric acid (50 ml.) to precipitate 3.24 g. of [1-oxo-2-(4-bromophenyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid which melts at 171°-172° C. after crystallization from nitromethane followed by acetic acid: water, 3:2.

Workup

  1. temperatureis warmed at 55°-60° C. for 3 hours
  2. additionThe reaction mixture is added slowly
  3. customto precipitate 3.24 g
  4. customof [1-oxo-2-(4-bromophenyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid which melts at 171°-172° C. after crystallization from nitromethane

Sources & evidence

ORD record
ord-3b7933c0fecd47abb209147280a5469a
Source dataset
uspto-grants-1979_12
Patent number
US04177285

Reaction notes

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