Dimethylformamide → 4-Bromo-3-fluorothiophenol

A stirred ice-cooled solution of triphenylphosphine (23.0 g, 87.7 mmol), in CH2Cl2 (50 mL) and DMF (1.6 mL) was treated with a solution of 4-bromo-3-fluorobenzene-1-sulfonyl chloride (8.00 g, 29.2 mmol) in CH2Cl2 (50 mL) and stirred room temperature for 16 hours. The mixture was washed with 1N aqueous HCl (80 mL) and concentrated in vacuo. The resulting solid was diluted with 1N aqueous NaOH (160 mL), the solid filtered and the filtrate washed with 2-methoxy-2-methylpropane (3×150 mL) and acidified to pH 1 with 1M aqueous HCl. Extraction of the aqueous layer with 2-methoxy-2-methylpropane (3×100 mL), followed by drying over sodium sulphate and concentrating in vacuo gave the title compound as a yellow oil 66% yield, 3.97 g.

1. washThe mixture was washed with 1N aqueous HCl (80 mL)
2. concentrationconcentrated in vacuo
3. additionThe resulting solid was diluted with 1N aqueous NaOH (160 mL)
4. filtrationthe solid filtered
5. washthe filtrate washed with 2-methoxy-2-methylpropane (3×150 mL)
6. extractionExtraction of the aqueous layer with 2-methoxy-2-methylpropane (3×100 mL)
7. dry with materialby drying over sodium sulphate
8. concentrationconcentrating in vacuo

ORD record

ord-7e3928262a194256aae8b1fd9b3e241b

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952008B2