Hydrochloric Acid → 3,4,4-Trifluoro-3-butenoic acid, 4-nitrophenyl ester

HRID 54733

반응식

HRID 54733 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[F:11][C:12](=[C:17]([F:19])[F:18])[CH2:13][C:14](Cl)=[O:15].C(N(CC)CC)C.Cl>CCOCC>[F:11][C:12](=[C:17]([F:19])[F:18])[CH2:13][C:14]([O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)=[O:15]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 9804-NitrophenolHCID 8471TriethylamineHCID 109207893,4,4-Trifluoro-3-butenoyl chloride

생성물 1

HCID 152391903,4,4-Trifluoro-3-butenoic acid, 4-nitrophenyl ester수율 92.1%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

A solution of 4-nitrophenol (1.10 g, 0.0079 mole) and 3,4,4-trifluoro-3-butenoyl chloride (1.85 g, 0.0116 mole) in dry ether (15 mL) is treated dropwise with triethylamine (1.01 g, 0.01 mole) at -78° C. with stirring. The mixture is stirred at -78° C. for 10 min and allowed to reach room temperature. The reaction mixture is diluted with ether (20 mL), stirred with 15 mL of 2 N HCl. The organic layer is successively washed with water, 5% sodium bicarbonate, brine, and dried. The dark brown residue obtained after evaporation of the solvent was purified by passing through a short column of silica gel to give 1.9 g of the product as a brown solid, a 91% yield. m.p. 58°-62° C.

후처리

  1. stirringThe mixture is stirred at -78° C. for 10 min
  2. customto reach room temperature
  3. washThe organic layer is successively washed with water, 5% sodium bicarbonate, brine
  4. customdried
  5. customThe dark brown residue obtained
  6. customafter evaporation of the solvent
  7. customwas purified

출처 및 근거

ORD 기록
ord-760aa76627d84edfb1a7dfe8d27792cc
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05623084

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