Ethyl Acetate → S-(2-Trimethylsilylethyl)-3-fluoro-5-phenylthiophenol

HRID 1901112Notes

Reaction equation

[H-].[Na+].[CH3:3][Si:4]([CH3:9])([CH3:8])[CH2:5][CH2:6][SH:7].[F:10][C:11]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:14]=[C:13](F)[CH:12]=1.C(OCC)(=O)C>CN(C=O)C>[CH3:3][Si:4]([CH3:9])([CH3:8])[CH2:5][CH2:6][S:7][C:13]1[CH:14]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:16]=[C:11]([F:10])[CH:12]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a suspension of NaH (360 mg) in DMF (10 mL) at 0° C. was added 2-(trimethylsilyl)ethanethiol (1.8 mL). After 10 min., a solution of 1,3-difluoro-5-phenylbenzene (1.9 g) in DMF (5 mL) was added and the resulting mixture was heated at 110° C. for 2.5 h. Ethyl acetate was added and the solution was washed with 1N HCl, H2O and brine. Concentration and chromatography (silica gel; hexane/EtOAc (98:2)) provided the title compound as a liquid.

Workup

washthe solution was washed with 1N HCl, H2O and brine
concentrationConcentration and chromatography (silica gel; hexane/EtOAc (98:2))

Sources & evidence

ORD record: ord-b5f33523b9b84f7daf7281a35877f702
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05576338

Reaction notes

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