Water → HCID 69037550, compound

HRID 853143Notes

Reaction equation

[F:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].O>CC(=O)CC>[CH2:28]([O:27][C:25](=[O:26])[CH2:24][O:14][C:11]1[CH:12]=[CH:13][C:8]([O:7][CH2:6][C:5]2[CH:15]=[CH:16][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:9][CH:10]=1)[CH3:29]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 3 g of 4-(4-fluoro-benzyloxy)-phenol in 40 ml of 2-butanone was treated with 2.5 g potassium carbonate and 1.6 ml of ethyl bromoacetate. The mixture was stirred at 80° C. during 3 h, then, in order to complete the reaction, 1.7 g of potassium carbonate and 1.9 ml of ethyl bromoacetate were added successively in four portions during a period of 24 h. For the working-up, the reaction mixture was cooled to room temperature, then treated with water and extracted with ethyl acetate. The organic layer was separated, dried over magnesium sulphate and evaporated under reduced pressure. There were obtained 2.95 g (71% of theory) of [4-(4-fluoro-benzyloxy)-phenoxy]-acetic acid ethyl ester as brownish crystals which were pure enough to be used in the next step without further purification; MS: m/e=304 (M)+.

Workup

additionwere added successively in four portions during a period of 24 h
temperaturethe reaction mixture was cooled to room temperature
extractionextracted with ethyl acetate
customThe organic layer was separated
dry with materialdried over magnesium sulphate
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-7f03b3bce3024abc8492bc56697e7b41
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253318B2

Reaction notes

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