4-Hydroxybenzaldehyde → 4-(2,2,3,3,3-Pentafluoropropoxy)benzaldehyde

HRID 16481

반응식

HRID 16481 반응식
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CC1C=CC(S(O[CH2:27][C:28]([F:34])([F:33])[C:29]([F:32])([F:31])[F:30])(=O)=O)=CC=1>CN(C=O)C.C(OCC)(=O)C>[F:33][C:28]([F:34])([C:29]([F:32])([F:31])[F:30])[CH2:27][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 27760172,2,3,3,3-Pentafluoropropyl p-Toluenesulfonate

생성물 1

HCID 866134424-(2,2,3,3,3-Pentafluoropropoxy)benzaldehyde수율 30.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 4-hydroxybenzaldehyde (2 g, 16.7 mmol) in DMF (33 mL) was stirred as solid potassium carbonate (4.1 g, 29.7 mmol) was added, and the reaction mixture was then stirred at RT. After 30 min, solid 2,2,3,3,3-pentafluoropropyl 4-methylbenzenesulfonate (5 g, 16.4 mmol) was added into the reaction mixture. The mixture was stirred and heated at 100° C. for 7 h. The reaction mixture was allowed to cool, diluted with ethyl acetate, washed with water (3×) and brine, and concentrated. Purification by flash chromatography on silica gel using a gradient of ethyl acetate in hexane afforded 4-(2,2,3,3,3-pentafluoropropoxy)benzaldehyde (1.26 g).

후처리

  1. additionwas added
  2. stirringThe mixture was stirred
  3. temperatureheated at 100° C. for 7 h
  4. temperatureto cool
  5. washwashed with water (3×) and brine
  6. concentrationconcentrated
  7. customPurification by flash chromatography on silica gel using a gradient of ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-6643a3580d464da8982c76918c38200a
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737145B2

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