Methanol → ((4-Bromobenzyl)oxy)acetic acid

Temperature

0 °C

To a flask containing NaH (1 g, 25 mmol) in dry THF (25 mL) at 0° C., was added a solution of 4-bromobenzyl alcohol (2.11 g, 11.3 mmol) in dry THF (10 mL). The solution was stirred at 0° C. for 1 h, then a solution of bromoacetic acid (1 g, 7.14 mmol) in dry THF (10 mL) was added. The solution was refluxed for 3 h, then cooled. A solution of MeOH (1 mL) in water (100 mL) was added, and mixture was extracted with EtOAc (2×20 mL). The water layer was acidified by 1N HCl to pH=2, then extracted with EtOAc (2×20 mL). The combined organic layer was washed with brine, dried (Na2SO4) and concentrated to give 67A. (1.66 g, 95%). MS (ESI) m/z 169.0 (M-OCH2CO2 H)+.

1. temperatureThe solution was refluxed for 3 h
2. temperaturecooled
3. extractionmixture was extracted with EtOAc (2×20 mL)
4. extractionextracted with EtOAc (2×20 mL)
5. washThe combined organic layer was washed with brine
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated

ORD record

ord-e1fbf3c524bc4b15b7166cf1a24cd660

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07592331B2