3-Bromophenol → 2-(3-Bromophenoxy)-2-methylpropanal

Cetyltrimethyl ammonium bromide (0.28 g, 0.77 mmol) was added to a solution of 3-bromophenol (6.66 g, 38.5 mmol) in 3.85M aqueous sodium hydroxide solution (10 ml), followed by a solution of 1,1-dichloro-2-hydroxy-2-methylpropane (A) (1.37 g, 9.6 mmol) in ether (20 ml). The mixture was stirred under an argon atmosphere for 18 hours then diluted with ether (50 ml), and extracted with 2M aqueous sodium hydroxide solution (4×30 ml), to remove unreacted phenol. The combined aqueous extracts were extracted with ether (50 ml), and the organic phase was washed with 2M aqueous sodium hydroxide solution (20 ml) followed by water (50 ml). The combined organic extracts were dried (MgSO4), concentrated, and purified by flash column chromatography, eluting with ethyl acetate/hexane (1:10 v/v), to give 2-(3-bromophenoxy)-2-methylpropanal (0.89 g), as an oil; NMR: 1.45(6H,s), 6.75-7.20(4H,m), 9.8(1H,s).

1. extractionextracted with 2M aqueous sodium hydroxide solution (4×30 ml)
2. customto remove unreacted phenol
3. extractionThe combined aqueous extracts were extracted with ether (50 ml)
4. washthe organic phase was washed with 2M aqueous sodium hydroxide solution (20 ml)
5. dry with materialThe combined organic extracts were dried (MgSO4)
6. concentrationconcentrated
7. custompurified by flash column chromatography
8. washeluting with ethyl acetate/hexane (1:10 v/v)

ORD record

ord-e7f7d0d0779048c0bd84a584b3e962b0

Source dataset

uspto-grants-1992_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05169974