1,3-Dibromopropane → HCID 57523451, compound

Temperature

0 °C

NaH at 60% in mineral oil (1.63 g, 40.8 mmol. 1.3 eq) was washed three times with hexane and subsequently dried. After addition of dried THF (30 mL) the suspension was cooled to 0° C. Dimethyl methylmalonate (4.7 g, 32.3 mmol, 1.0 eq) was slowly and carefully added and gas development was observed. The mixture was stirred for 15 minutes and subsequently 1,3-dibromopropane (24 g, 119.0 mmol, 3.7 eq) was added in one portion. The mixture was allowed to reach room temperature and was then stirred for further 16 hours. NaOH 1.0 M solution was added, the crude was extracted with ethyl acetate; the organic layers were collected and dried, the obtained oil was purified by SiO2 column (elution: cyclohexane followed by EtOAc). The title product (6.6 g, 76% yield) was obtained.

1. washNaH at 60% in mineral oil (1.63 g, 40.8 mmol. 1.3 eq) was washed three times with hexane
2. customsubsequently dried
3. additionAfter addition of dried THF (30 mL) the suspension
4. additioncarefully added
5. customto reach room temperature
6. stirringwas then stirred for further 16 hours
7. extractionthe crude was extracted with ethyl acetate
8. customthe organic layers were collected
9. customdried
10. customthe obtained oil was purified by SiO2 column (elution: cyclohexane followed by EtOAc)

ORD record

ord-3852d707e94f41aba7d4f1920418a61d

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08163729B2