Reaction #75564

Reaction equation

2-bromomethyl-benzonitrile

2-methoxy-5-bromo-thiophenol

2-methoxy-5-bromo-thiophenol

K2CO3

→

product

Yield 64.9%

2-(5-Bromo-2-methoxy-phenylsulfanylmethyl)-benzonitrile

Yield 64.9%

Solvents

DMF

DMF

water

Conditions

Workup

1. 1
   OtherThe reaction was capped
2. 2
   Temperatureheated to 40° C. for 12 hours
3. 3
   Extractionextracted with ethyl acetate (2×10 mL)
4. 4
   WashThe organic extracts were washed with water (3×10 mL), brine (2×10 mL)
5. 5
   Dryingdried (Na2SO4)
6. 6
   OtherThe solvent was evaporated
7. 7
   Otherthe product was purified on silica gel (eluting with 9:1 of hexane/ethyl acetate)

Procedure

As depicted in Scheme 7 above, to a solution of 104 mg (0.470 mmol) of 2-methoxy-5-bromo-thiophenol in 5 mL of DMF was added 162 mg (1.18 mmol) of anhydrous to a solution of 104 mg (0.470 mol) of 2-methoxy-5-bromo-thiophenol in 5 mL of DMF was added 162 mg (1.18 mol) of anhydrous K2CO3. The solution was stirred for 15 minutes at 22° C. and 103 mg (0.520 mmol) of 2-bromomethyl-benzonitrile was added. The reaction was capped and heated to 40° C. for 12 hours. The mixture was subsequently diluted with 5 mL of water and extracted with ethyl acetate (2×10 mL). The organic extracts were washed with water (3×10 mL), brine (2×10 mL), and dried (Na2SO4). The solvent was evaporated and the product was purified on silica gel (eluting with 9:1 of hexane/ethyl acetate) to afford 102 mg of the product as a colorless oil.

Source