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

HRID 1392364
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HRID 1392364 반응식
[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
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참가 물질

7

반응물 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 707414-BromobenzaldehydeHCID 882092,4-Dichlorophenylacetic acid

생성물 1

HCID 692887223-(4-Bromophenyl)-2-(2,4-dichlorophenyl)acrylic acid수율 53%

시약·촉매·용매 2

HCID 962Water용매
HCID 8857Ethyl Acetate용매

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온도
110 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-6e4c371a58204fd68df13f4e828842ed
출처 데이터셋
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07342032B2

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