Bromoacetic Acid → 2-(1-(4-Bromophenyl)cyclopentyloxy)acetic acid

To an ambient suspension of NaH (332 mg, 8.30 mmol, 60 wgt % in mineral oil) in N,N-dimethylformamide (2 mL) was added dropwise a solution of Example 30A (1.0 g, 4.15 mmol) in N,N-dimethylformamide (1 mL). After 30 min., bromoacetic acid (577 mg, 4.15 mmol) in N,N-dimethylformamide (13 mL) was added, dropwise. The solution was stirred at room temperature for 16 h and then heated to 50° C. for 3 h. The reaction was cooled to room temperature and was quenched by the addition of water (10 mL). The solution was basicified to pH 10 by the addition of 2.5 M NaOH. The aqueous was extracted with ethyl acetate (2×10 mL), and the organics discarded. The aqueous was acidified to pH 1 with 6 M HCl, and then extracted with ethyl acetate (3×10 mL). The combined organics were washed with water (3×10 mL), brine (1×10 mL), dried over sodium sulfate, filtered, and concentrated, under reduced pressure to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.66-1.72 (m, 2 H), 1.74-1.85 (m, 4 H), 2.02-2.15 (m, 2 H), 3.56-3.60 (m, 2 H), 7.33-7.39 (m, 2 H), 7.49-7.56 (m, 2 H), 12.37 (s, 1 H).

1. temperatureheated to 50° C. for 3 h
2. temperatureThe reaction was cooled to room temperature
3. customwas quenched by the addition of water (10 mL)
4. additionThe solution was basicified to pH 10 by the addition of 2.5 M NaOH
5. extractionThe aqueous was extracted with ethyl acetate (2×10 mL)
6. extractionextracted with ethyl acetate (3×10 mL)
7. washThe combined organics were washed with water (3×10 mL), brine (1×10 mL)
8. dry with materialdried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated, under reduced pressure

ORD record

ord-e332745ffef84ba7ab0b961972adabaf

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08901152B2