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

HRID 274781Notes

Reaction equation

HRID 274781 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

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 2N 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.

Workup

  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

Sources & evidence

ORD record
ord-c9a786369d0a4c0b9a3591a8b5e36ab7
Source dataset
uspto-grants-1995_02
Patent number
US05389680

Reaction notes

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