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

HRID 29670노트

반응식

HRID 29670 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5048116a362c4164b57cae7268d35d05
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07420083B2

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