Iodoethane → (3-Bromo-4-fluorophenyl)(ethyl)sulfane

HRID 575570Notes

Reaction equation

HRID 575570 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([SH:9])[CH:5]=[CH:6][C:7]=1[F:8].C([O-])([O-])=O.[K+].[K+].[CH2:16](I)[CH3:17]>CC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([S:9][CH2:16][CH3:17])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 265970903-Bromo-4-Fluorothiophenol

Product 1

HCID 86704956(3-Bromo-4-fluorophenyl)(ethyl)sulfaneYield 99.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 3-bromo-4-fluorobenzenethiol (2.07 g, 10 mmol) and K2CO3 (4.14 g, 30 mmol) in acetone (20 mL) was added EtI (3.12 g, 20 mmol). The mixture was stirred at room temperature for 12 h, filtered, and the volatile components were removed under vacuum to give the title compound (2.34 g) as light yellow oil which was carried on without purification. 1H NMR (CDCl3, 400 MHz): d 7.54 (dd, J1=6.4 Hz, J2=2.4 Hz, 1H), 7.26-7.25 (m, 1H), 7.05 (t, J=8.4 Hz, 1H), 2.91 (q, J=7.6 Hz, 2H), 1.30 (t, J=7.6 Hz, 3H).

Workup

  1. filtrationfiltered
  2. customthe volatile components were removed under vacuum

Sources & evidence

ORD record
ord-be3f264a58ac46359496890cf9d93961
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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