Hydrogen Bromide → Ethyl 4-bromo-2,2-dimethylbutanoate

Hydrogen bromide was bubbled through 3,3-dimethyldihydro-2(3H)-furanone (1 g, 8.76 mmol) at room temperature for ca. 5 h and the resulting mixture was left at room temperature overnight. Nitrogen was then bubbled through the mixture. The crude acid was dissolved in DCM (10 ml) and treated with oxalyl chloride (2.3 ml, 26.3 mmol) and DMF (1 drop) and the resulting mixture was stirred at room temperature over the weekend then concentrated in vacuo. The residue was treated with ethanol (10 ml) and the resulting mixture stirred at room temperature for 1 hour then poured into water. The aqueous phase was extracted twice with diethyl ether and the ethereal solution was washed with brine, dried and concentrated in vacuo to give the title compound (949 mg, 49%) as a very pale yellow oil which was used in the next step without further purification.

1. customNitrogen was then bubbled through the mixture
2. dissolutionThe crude acid was dissolved in DCM (10 ml)
3. concentrationthen concentrated in vacuo
4. additionThe residue was treated with ethanol (10 ml)
5. stirringthe resulting mixture stirred at room temperature for 1 hour
6. additionthen poured into water
7. extractionThe aqueous phase was extracted twice with diethyl ether
8. washthe ethereal solution was washed with brine
9. customdried
10. concentrationconcentrated in vacuo

ORD record

ord-513410853994469ba69268a180550caf

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08324254B2