2-Chlorooctane → Methyl 4-Bromo-5-chloro-2-furoate

Temperature

-78 °C

Isopropylmagnesium chloride (1.20 ml, 2.40 mmol) was added dropwise to a solution of methyl 4,5-dibromo-2-furancarboxylate (568 mg, 2.0 mmol) in Tetrahydrofuran (THF) (16 ml) at 0° C. The resulting mixture was stirred at this temperature for 30 min and then cooled to −78° C. A solution of hexylchloroethane (568 mg, 2.401 mmol) in THF (1 mL) was added dropwise, and the resulting mixture was stirred at this temperature for 1 hr. The reaction was quenched with addition of NH4Cl (sat. aq) and the resulting mixture was stirred at rt overnight. Ether and water were added and the aqueous layer was discarded. The organic layer was washed with brine, dried (Na2SO4) and concentrated to give 0.34 g of the product containing its isopropyl ester.

1. stirringthe resulting mixture was stirred at this temperature for 1 hr
2. customThe reaction was quenched with addition of NH4Cl (sat. aq)
3. stirringthe resulting mixture was stirred at rt overnight
4. additionEther and water were added
5. washThe organic layer was washed with brine
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated

ORD record

ord-967ee81df631464a89e053751594b713

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08273782B2