Water → 2-[2-(4-Fluorophenylthio)-6-fluorophenyl]-4,4-dimethyloxazoline

HRID 1974754Notes

Reaction equation

HRID 1974754 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.C([Li])CCC.[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17](F)[C:16]=1[C:22]1[O:23][CH2:24][C:25]([CH3:28])([CH3:27])[N:26]=1.O>C1COCC1.CCCCCC.CCCCCC.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([F:14])[C:16]=2[C:22]2[O:23][CH2:24][C:25]([CH3:28])([CH3:27])[N:26]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 677894-FluorothiophenolHCID 10987554Oxazole, 2-(2,6-difluorophenyl)-4,5-dihydro-4,4-dimethyl-HCID 178418339Butyllithium

Product 1

HCID 191022272-[2-(4-Fluorophenylthio)-6-fluorophenyl]-4,4-dimethyloxazoline

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a solution of 4-fluorothiophenol (3.64 g, 28.4 mmol) in 50 ml of dry THF at -78° C. is added n-butyllithium (17.8 ml of a 1.6M solution in hexane). After 30 minutes, 2-(2,6-difluorophenyl)-4,4-dimethyloxazoline (5.0 g, 23.7 mmol) in 10 ml of dry THF is added dropwise. The reaction mixture is allowed to warm to room temperature and then is heated to 60° C. for 5.5 hours. After cooling, the reaction mixture is poured into water and then extracted with diethyl ether. The extracts are washed with water and then brine, and dried over MgSO4 to afford the crude product. Chromatography over silica gel eluting with 10:1 hexane/ethyl acetate afforded the subtitle compound.

Workup

  1. temperatureis heated to 60° C. for 5.5 hours
  2. temperatureAfter cooling
  3. extractionextracted with diethyl ether
  4. washThe extracts are washed with water
  5. dry with materialbrine, and dried over MgSO4
  6. customto afford the crude product

Sources & evidence

ORD record
ord-78cc4601d37542bb80103bc8d873152a
Source dataset
uspto-grants-1994_02
Patent number
US05283361

Reaction notes

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