Acetic Anhydride → 3-(4-Bromophenyl)-2-(2,4-dichlorophenyl)acrylic acid

HRID 1392364Notes

Reaction equation

[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[CH2:18][C:19]([OH:21])=[O:20].C(OC(=O)C)(=O)C.C(N(CC)CC)C>C(OCC)(=O)C.O>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[C:18]([C:12]2[CH:13]=[CH:14][C:15]([Cl:17])=[CH:16][C:11]=2[Cl:10])[C:19]([OH:21])=[O:20])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

Part A; To 4-bromobenzaldehyde (25 gram, 0.135 mol) is successively added 2,4-dichlorophenylacetic acid (27.7 gram, 0.135 mol), acetic anhydride (100 mL) and triethylamine (19 mL, 0.136 mol) and the resulting mixture is heated at reflux temperature for 90 minutes. The reaction mixture is cooled to 110° C. and water (100 mL) is slowly added. The resulting mixture is allowed to attain room temperature and ethyl acetate is added. The ethyl acetate layer is twice washed with water, dried over MgSO4, filtered and concentrated in vacuo. The resulting oil is crystallised from diisopropyl ether to give 3-(4-bromophenyl)-2-(2,4-dichlorophenyl)acrylic acid as a white solid (26.55 gram, 53% yield).

Workup

temperaturethe resulting mixture is heated
temperatureat reflux temperature for 90 minutes
customto attain room temperature
washThe ethyl acetate layer is twice washed with water
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe resulting oil is crystallised from diisopropyl ether

Sources & evidence

ORD record: ord-6e4c371a58204fd68df13f4e828842ed
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07342032B2

Reaction notes

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