Ethanol → Ethyl 3-(2,4-difluorophenylthio)-4-nitrobenzoate

HRID 1087174Notes

Reaction equation

HRID 1087174 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]=1[N+:19]([O-:21])=[O:20])[C:13]([OH:15])=[O:14].[CH2:22](O)[CH3:23]>Cl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]=1[N+:19]([O-:21])=[O:20])[C:13]([O:15][CH2:22][CH3:23])=[O:14]

Participants

4

Reactant 2

HCID 702EthanolHCID 100867683-(2,4-Difluorophenylthio)-4-nitrobenzoic acid

Product 1

HCID 10359815Ethyl 3-(2,4-difluorophenylthio)-4-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 3-(2,4-difluorophenylthio)-4-nitrobenzoic acid (1.2 g) in 20% hydrogen chloride in ethanol (3 ml) was refluxed for 2 hours. The mixture was concentrated. The residue was dissolved in ethyl acetate and washed with an aqueous solution of sodium bicarbonate and water successively. The extract was evaporated and the residual oil was crystallized from a mixture of hexane and ethanol to give crystals of ethyl 3-(2,4-difluorophenylthio)-4-nitrobenzoate (1.1 g).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with an aqueous solution of sodium bicarbonate and water successively
  4. customThe extract was evaporated
  5. customthe residual oil was crystallized from a mixture of hexane and ethanol

Sources & evidence

ORD record
ord-21550f48741d48fda2cb1c5a0abf243d
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

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