4-Bromophenol → HCID 178419397, compound

To a mixture of liquid 4-bromophenol (25 g, mp 64-68° C.) at 100-110° C. and its sodium salt [Prepared from 3.5 g (20 mmol) 4-bromo-phenol and sodium metal (0.46 g, 20 mmol) in anhydrous methanol. The resultant solution was concentrated and the residual solvent removed under vacuum overnight], neat methyl N-(cyano-methyl)methanimidate (2 mL, 20 mmol; Hosmane, R. S. et al, J. Org. Chem., p. 1212, 1984) was added dropwise over a period of 10 minutes under a slow stream of dry argon. The resultant mixture was stirred at 100° C. for 2 h, and the reaction product partitioned between methylene chloride (250 mL) and aqueous sodium hydroxide (1 M, 250 mL). The aqueous layer was separated and extracted with methylene chloride (3×50 mL). The organic extracts were combined, washed with brine (50 mL), dried over anhydrous potassium carbonate, filtered and concentrated. The residue was subjected to column chromatography on silica gel eluting with a mixture of 7:3 v/v chloroform and acetone. Collection and concentration of appropriate fractions provided the titled compound as white powder.

1. concentrationThe resultant solution was concentrated
2. additionwas added dropwise over a period of 10 minutes under a slow stream of dry argon
3. customthe reaction product partitioned between methylene chloride (250 mL) and aqueous sodium hydroxide (1 M, 250 mL)
4. customThe aqueous layer was separated
5. extractionextracted with methylene chloride (3×50 mL)
6. washwashed with brine (50 mL)
7. dry with materialdried over anhydrous potassium carbonate
8. filtrationfiltered
9. concentrationconcentrated
10. additionThe residue was subjected to column chromatography on silica gel eluting with a mixture of 7:3 v/v chloroform and acetone
11. customCollection and concentration of appropriate fractions

ORD record

ord-d1cb2a98f0204e3487e4800071327d49

Source dataset

uspto-grants-2000_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06093737