Water → Benzo(b)thiophene, 3-bromo-

A solution of bromine (20.4 ml, 0.40 mole) in chloroform (100 ml) was added dropwise over 1 hour to a stirred mixture of benzothiophene (53.6 g, 0.40 mole) and anhydrous sodium acetate (54.4 g, 0.68 mole) in chloroform (300 ml) at room temperature. The reaction mixture became much thicker during the addition, so a further 300 ml of chloroform was added to aid stirring. After completing the addition, the reaction mixture was stirred for a further 2 hours and then water added (200 ml) to dissolve the inorganic solid. The chloroform layer was separated and washed with water (1×200 ml), sodium hydrogen carbonate solution (1×200 ml) and brine (1×200 ml); then dried (MgSO4) and evaporated to dryness to give a quantitative yield of the title compound as a yellow oil.

1. additionThe reaction mixture became much thicker during the addition
2. additionthe addition
3. stirringthe reaction mixture was stirred for a further 2 hours
4. dissolutionto dissolve the inorganic solid
5. customThe chloroform layer was separated
6. washwashed with water (1×200 ml), sodium hydrogen carbonate solution (1×200 ml) and brine (1×200 ml)
7. dry with materialthen dried (MgSO4)
8. customevaporated to dryness

ORD record

ord-4b30c107aff244dd87f637f98b7bd6b7

Source dataset

uspto-grants-1985_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04548948