Water → (4-Bromo-3-fluorophenyl)(cyclobutyl)sulfane

HRID 1846019Notes

Reaction equation

HRID 1846019 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][C:3]=1[F:9].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH:17]1[CH2:20][CH2:19][CH2:18]1.O>CS(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:17]2[CH2:20][CH2:19][CH2:18]2)=[CH:4][C:3]=1[F:9]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 78110BromocyclobutaneHCID 265970934-Bromo-3-fluorothiophenol

Product 1

HCID 86723241(4-Bromo-3-fluorophenyl)(cyclobutyl)sulfaneYield 95.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

A stirred mixture of 4-bromo-3-fluorobenzenethiol (Preparation 26, 400 mg, 1.93 mmol), cesium carbonate (691 mg, 2.12 mmol) and bromocyclobutane (287 mg, 2.12 mmol) in DMSO (8 mL) was heated at 70° C. for 19 hours. The mixture was cooled to room temperature, poured into water (30 mL) and extracted with 2-methoxy-2-methylpropane (30 mL), washed with water (30 mL), dried over sodium sulfate and concentrated in vacuo. This gave the title compound as a colourless oil 95% yield, 480 mg.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with 2-methoxy-2-methylpropane (30 mL)
  3. washwashed with water (30 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c968ea0182dc4b52b0e8ea1f4632b8fd
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

Loading…