2-Bromophenol → HCID 21914329, compound

1-Ethyl-3-pyrrolidinol (0.5 ml), 2-bromophenol (0.37 ml) and triphenylphosphine (1.02 g) were dissolved in tetrahydrofuran (10 ml) and the mixture cooled in an ice bath before dropwise addition of diisopropyl azodicarboxylate (0.77 ml). The mixture was allowed to warm to room temperature over 3 h. The mixture was concentrated in vacuo and partitioned between ether (50 ml) and water (50 ml) and the aqueous phase was extracted further with ether (50 ml). The combined organic phases were washed with water (2×25 ml), brine (2×25 ml), dried (MgSO4) and concentrated in vacuo. The product was dissolved in ethyl acetate (50 ml) and extracted with 2M aqueous hydrochloric acid (3×20 ml). The aqueous washings were combined and basified by the addition of solid sodium hydroxide and extracted with ethyl acetate (3×20 ml), dried (MgSO4) and concentrated in vacuo. The residue was purified by cation exchange chromatography eluting with ammonia/methanol/dichloromethane mixtures. This gave the title compound as a pale orange oil (529 mg).

1. concentrationThe mixture was concentrated in vacuo
2. custompartitioned between ether (50 ml) and water (50 ml)
3. extractionthe aqueous phase was extracted further with ether (50 ml)
4. washThe combined organic phases were washed with water (2×25 ml), brine (2×25 ml)
5. dry with materialdried (MgSO4)
6. concentrationconcentrated in vacuo
7. dissolutionThe product was dissolved in ethyl acetate (50 ml)
8. extractionextracted with 2M aqueous hydrochloric acid (3×20 ml)
9. additionbasified by the addition of solid sodium hydroxide
10. extractionextracted with ethyl acetate (3×20 ml)
11. dry with materialdried (MgSO4)
12. concentrationconcentrated in vacuo
13. customThe residue was purified by cation exchange chromatography
14. washeluting with ammonia/methanol/dichloromethane mixtures

ORD record

ord-a219e116d2e949ef88dc2b27f2693193

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07956084B2