1,4-Dibromobenzene → 1-(4-Bromophenyl)cyclobutanol

Temperature

-78 °C

A flame dried flask under N2 was charged with 1,4-dibromobenzene (7.52 g, 31.9 mmol) and anhydrous THF (50 mL). The reaction mixture was cooled to −78° C. and 2.5 M n-BuLi in hexanes (12.8 mL, 32 mmol) was added keeping the temperature below −60° C. The reaction mixture was stirred-at −78° C. for 30 min and then cyclobutanone (2 mL, 26.8 mmol) was added slowly keeping the temp below −60° C. After one hour, the reaction was poured into a saturated NH4Cl solution (40 mL). The salts were filtered through Celite™ and washed with EtOAc (2×20 mL). The layers were separated and the aq. phase was extracted with additional EtOAc (20 mL). The combined organic layers were washed with brine, dried (Na2SO4) and concentrated to a pale yellow oil (5.51 g). The material could be used without further purification. 13C NMR (400 MHz, CDCl3) d 145.5, 131.7, 127.1, 121.3, 76.8, 37.2, 13.2; MS (AP/Cl) 209.0, 211.0 (M+H—H2O)+.

1. customA flame dried flask under N2
2. customthe temperature below −60° C
3. customthe temp below −60° C
4. waitAfter one hour
5. filtrationThe salts were filtered through Celite™
6. washwashed with EtOAc (2×20 mL)
7. customThe layers were separated
8. extractionthe aq. phase was extracted with additional EtOAc (20 mL)
9. washThe combined organic layers were washed with brine
10. dry with materialdried (Na2SO4)
11. concentrationconcentrated to a pale yellow oil (5.51 g)
12. customThe material could be used without further purification

ORD record

ord-5676ad5152584ff3af0bfeff84bad9eb

Source dataset

uspto-grants-2009_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07479559B2