Phosphorus tribromide → 3-(Bromomethyl)-2,5-dichlorothiophene

To a solution of (2,5-dichlorothiophen-3-yl)methanol (280 mg, 1.5 mmol) in anhydrous dichloromethane (15 mL) was added dropwise phosphorus tribromide (285 μL, 3.0 mmol). The mixture was stirred at room temperature for 3 hours. Dichloromethane was evaporated. The residue was treated with a saturated sodium bicarbonate solution until no more gas evolved. The resultant mixture was extracted with EtOAc (3×20 mL). The organic extracts were combined, dried over MgSO4, filtered, evaporated, and dried in vacuo, affording 3-(bromomethyl)-2,5-dichlorothiophene (125 mg, 34% yield). The product was used without further purification.

1. customDichloromethane was evaporated
2. additionThe residue was treated with a saturated sodium bicarbonate solution until no more gas
3. extractionThe resultant mixture was extracted with EtOAc (3×20 mL)
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. customevaporated
7. customdried in vacuo

ORD record

ord-191e930e2b914a559e89c70e20d87c29

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09040538B2