1,3-Dibromopropane → 2-(3,5-Bis-trifluoromethyl-benzoylamino)-4-(3-bromo-propoxy)-benzoic acid methyl ester

HRID 29670ノート

反応式

HRID 29670 の反応式
[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[NH:11][C:12](=[O:27])[C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]([C:23]([F:26])([F:25])[F:24])[CH:14]=1.[Br:29][CH2:30][CH2:31][CH2:32]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:32][CH2:31][CH2:30][Br:29])=[CH:6][C:5]=1[NH:11][C:12](=[O:27])[C:13]1[CH:14]=[C:15]([C:23]([F:24])([F:25])[F:26])[CH:16]=[C:17]([C:19]([F:21])([F:22])[F:20])[CH:18]=1

参加物

5

反応物 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 865974002-(3,5-Bis-trifluoromethyl-benzoylamino)-4-hydroxy-benzoic acid methyl ester

生成物 1

HCID 865974012-(3,5-Bis-trifluoromethyl-benzoylamino)-4-(3-bromo-propoxy)-benzoic acid methyl ester収率 78%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a solution of 2-(3,5-bis-trifluoromethyl-benzoylamino)-4-hydroxy-benzoic acid methyl ester (10.10 g, 2.70 mmol) and 1,3-dibromopropane (2.18 g, 10.8 mmol) in acetone (75 mL) was added potassium carbonate (1.87 g, 13.5 mmol). The reaction mixture was heated to reflux for 3 hours and allowed to cool back down to room temperature. The mixture was partitioned between ethyl acetate and brine, and the layers were separated. The aqueous layer was extracted with one additional portion of ethyl acetate. The organics were combined, washed with one portion of brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude oil was purified by flash chromatography through silica gel using ethyl acetate/hexanes (0/100 gradient to 8/92) to give 2-(3,5-bis-trifluoromethyl-benzoylamino)-4-(3-bromo-propoxy)-benzoic acid methyl ester (1.11 g, 78%) as a white powder. 1H NMR (400 MHz, CDCl3); δ 12.58 (s, 1H), 8.53 (d, 1H), 8.51 (s, 2H), 8.08 (s, 1H), 8.04 (d, 1H), 6.70 (dd, 1H), 4.24 (t, 2H), 3.96 (s, 3H), 3.62 (t, 2H), 2.37 (m, 2H).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 hours
  3. customThe mixture was partitioned between ethyl acetate and brine
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted with one additional portion of ethyl acetate
  6. washwashed with one portion of brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude oil was purified by flash chromatography through silica gel

出典と根拠

ORDレコード
ord-5048116a362c4164b57cae7268d35d05
出典データセット
uspto-grants-2008_09
特許番号
US07420083B2

反応ノート

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