Ethyl bromoacetate → HCID 20373885, compound

HRID 1834689Notes

Reaction equation

[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([OH:9])[CH:5]=[CH:4][C:3]=1[C:10](=[O:16])[CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][C:25]([O:27]CC)=[O:26].[OH-].[K+]>CN(C)C=O.O>[Cl:8][C:7]1[C:2]([Cl:1])=[C:3]([C:10](=[O:16])[CH2:11][C:12]([CH3:13])([CH3:15])[CH3:14])[CH:4]=[CH:5][C:6]=1[O:9][CH2:24][C:25]([OH:27])=[O:26]

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 2',3'-dichloro-3,3-dimethyl-4'-hydroxybutyrophenone (15.5 g., 0.059 mole) and potassium carbonate (9.7 g., 0.070 mole) in dimethylformamide (DMF) (60 ml.) is stirred at 65° C. for 1/2 hour. Ethyl bromoacetate (11.7 g., 0.070 mole) is added in one portion and heating and stirring were continued for three hours. A solution of potassium hydroxide (4.6 g., 0.082 mole) in water (80 ml.) is added and the mixture is refluxed for 1/2 hour. The resulting semisolid mass is added to water (750 ml.). The solution is heated to boiling, filtered, cooled and acidified (HCl) to afford 18 g. of [2,3-dichloro-4-(3,3-dimethylbutyryl)phenoxy]acetic acid, m.p. 145°-145.5° C. after recrystallization from benzene.

Workup

temperatureheating
stirringstirring
waitwere continued for three hours
temperaturethe mixture is refluxed for 1/2 hour
temperatureThe solution is heated
filtrationfiltered
temperaturecooled
customto afford 18 g
customof [2,3-dichloro-4-(3,3-dimethylbutyryl)phenoxy]acetic acid, m.p. 145°-145.5° C. after recrystallization from benzene

Sources & evidence

ORD record: ord-c6c4f23dae7544e1ba3388960ebd164e
Source dataset: uspto-grants-1978_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04070539

Reaction notes

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