Ethyl bromoacetate → {[6,7-Dichloro-2-methyl-1-oxo-2-(propan-2-yl)-2,3-dihydro-1H-inden-5-yl]oxy}acetic acid

HRID 1679714Notes

Reaction equation

[CH3:1][C:2]1([CH:15]([CH3:17])[CH3:16])[CH2:10][C:9]2[C:4](=[C:5]([Cl:13])[C:6]([Cl:12])=[C:7]([OH:11])[CH:8]=2)[C:3]1=[O:14].C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][C:26]([O:28]CC)=[O:27].[OH-].[Na+]>CN(C=O)C.O>[O:14]=[C:3]1[C:4]2[C:9](=[CH:8][C:7]([O:11][CH2:25][C:26]([OH:28])=[O:27])=[C:6]([Cl:12])[C:5]=2[Cl:13])[CH2:10][C:2]1([CH3:1])[CH:15]([CH3:17])[CH3:16]

Participants

Conditions

Temperature: 55 °C

Procedure

A stirred mixture of 2-methyl-2-isopropyl-5-hydroxy-6,7-dichloro-1-indanone (6.2 g., 0.023 mole), potassium carbonate (7.3 g.), ethyl bromoacetate (8.5 g.) in DMF (70 ml.) is warmed in an inert atmosphere at 55° C. for 1 hour, then treated with water (60 ml.) and 10N sodium hydroxide (10 ml.) and heated on a steam bath for 1.5 hours. The reaction mixture is poured into water, acidified, extracted with ether, washed with water and dried over magnesium sulfate. Following evaporation of the ether there is obtained 5.1 g. of (1-oxo-2-methyl-2-isopropyl-6,7-dichloro-5-indanyloxy)acetic acid which melts at 156°-157° C. after recrystallization from nitromethane.

Workup

temperatureheated on a steam bath for 1.5 hours
extractionextracted with ether
washwashed with water
dry with materialdried over magnesium sulfate
customevaporation of the ether
customthere is obtained 5.1 g
customof (1-oxo-2-methyl-2-isopropyl-6,7-dichloro-5-indanyloxy)acetic acid which melts at 156°-157° C. after recrystallization from nitromethane

Sources & evidence

ORD record: ord-e651aed7cb6c4194a72b27cd3e2132ad
Source dataset: uspto-grants-1978_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04081554

Reaction notes

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