Dimethylformamide → 2-Chloromethylbenzofuran

Compound 4 (155.25 g) was dissolved in anhydrous ethyl ether (250 ml) containing dimethylformamide (1 ml). The reaction flask was placed into an ice bath, and when the solution temperature was between 0° C. and 4° C., thionyl chloride (124.3 g, 76.2 ml) was added dropwise, while stirring, over the period of 1 hour. The mixture was then stirred for another hour, washed with water (250 ml), 3% sodium bicarbonate solution (250 ml), and with water again (250 ml). The material was dried over magnesium sulfate, filtered, and the solvent evaporated. The product was distilled in vacuo, and the yield was approximately 117 g. The boiling point is about 78° C. at 1.5 mm Hg.

1. customThe reaction flask was placed into an ice bath
2. customwas between 0° C. and 4° C.
3. stirringThe mixture was then stirred for another hour
4. washwashed with water (250 ml), 3% sodium bicarbonate solution (250 ml)
5. dry with materialThe material was dried over magnesium sulfate
6. filtrationfiltered
7. customthe solvent evaporated
8. distillationThe product was distilled in vacuo

ORD record

ord-f05b0fa405544e4fb4deaba7b64487a3

Source dataset

uspto-grants-1994_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05364880