Potassium Carbonate → 1-Bromo-4-[(cyclopropylmethyl)thio]benzene

HRID 1698495Notes

Reaction equation

HRID 1698495 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH:15]1([CH2:18]Br)[CH2:17][CH2:16]1>CN(C)C=O.C(OCC)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:18][CH:15]2[CH2:17][CH2:16]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 660494-BromothiophenolHCID 81503Bromomethylcyclopropane

Product 1

HCID 579566301-Bromo-4-[(cyclopropylmethyl)thio]benzeneYield 95.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

4-Bromothiophenol (37.8 g) in N,N-dimethylformamide (200 mL) was treated with potassium carbonate (30.4 g) and cyclopropylmethyl bromide (29.7 g). The suspension was stirred at ambient temperature for 16 hrs then diluted with diethyl ether (500 mL). The organic phase was washed with water (2×500 mL), dried (MgSO4) and concentrated to give the title compound as an oil (46.4 g). 1H NMR (360 MHz, CDCl3): δ 7.38 (2H, d, J=8.0 Hz), 7.21 (2H, d, J=8.0 Hz), 2.83 (2H, d, J=7.0 Hz), 1.08-0.98 (1H, m), 0.58 (2H, q, J=5.1 Hz), 0.24 (2H, q, J=5.1 Hz).

Workup

  1. washThe organic phase was washed with water (2×500 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3df9611f900c4d408b342f78a704e653
Source dataset
uspto-grants-2012_04
Patent number
US08163956B2

Reaction notes

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