Ethyl Bromide → 1-ethylsulfanyl-4-fluorobenzene

HRID 968134Notes

Reaction equation

HRID 968134 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1.[CH2:11](Br)[CH3:12]>O.CO>[CH2:11]([S:10][C:7]1[CH:8]=[CH:9][C:4]([F:3])=[CH:5][CH:6]=1)[CH3:12]

Participants

6

Reactant 3

HCID 6332Ethyl BromideHCID 14798Sodium Hydroxide2×HCID 677894-Fluorothiophenol

Product 1

HCID 53241531-ethylsulfanyl-4-fluorobenzeneYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirring solution of NaOH (11.26 g, 281.6 mmol) in water (500 mL) was added dropwise a solution of 4-fluorothiophenol (25 mL, 234.6 mmol) in methanol (50 mL). After 15 minutes ethyl bromide (14.4 mL, 281.6 mmol) was added. After 6 hours more NaOH (1 g) was added and the reaction mixture was extracted with ether (3×300 mL). The combined organic extracts were treated with brine followed by MgSO4 then concentrated down to give 1-(ethylthio)-4-fluorobenzene (29 g, 80%) as a slightly yellow colored liquid.

Workup

  1. extractionthe reaction mixture was extracted with ether (3×300 mL)
  2. additionThe combined organic extracts were treated with brine
  3. concentrationthen concentrated down

Sources & evidence

ORD record
ord-38b039b602e24c13a8880f7b6c401818
Source dataset
uspto-grants-2005_10
Patent number
US06956052B2

Reaction notes

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