Water → 5-Bromo-2-hydroxybenzene-1,3-dicarbaldehyde

Temperature

120 °C

Hexamethylenetetramine (73.84 g, 526 mmol) was added to TFA (240 mL) with stirring. 4-Bromophenol (22.74 g, 131 mmol) was added in one portion and the solution heated in an oil bath to 120° C. and stirred under argon for 48 h. The reaction mixture was then cooled to ambient temperature. Water (160 mL) and 50% aqueous H2SO4 (80 mL) were added and the solution stirred for an additional 2 h. The reaction mixture was poured into water (1600 mL) and the resulting precipitate collected on a Büchner funnel. The precipitate was dissolved in ethyl acetate (EtOAc) and the solution was dried over MgSO4. The solution was filtered and the solvent removed on a rotary evaporator. Purification by column chromatography on silica gel (400 g) using a gradient of 15-40% ethyl acetate in hexanes resulted in a isolation of the product as a yellow solid (18.0 g, 60%).

1. stirringstirred under argon for 48 h
2. temperatureThe reaction mixture was then cooled to ambient temperature
3. stirringthe solution stirred for an additional 2 h
4. customthe resulting precipitate collected on a Büchner funnel
5. dissolutionThe precipitate was dissolved in ethyl acetate (EtOAc)
6. dry with materialthe solution was dried over MgSO4
7. filtrationThe solution was filtered
8. customthe solvent removed on a rotary evaporator
9. customPurification by column chromatography on silica gel (400 g)

ORD record

ord-fe3960871dcd4b44878f683c28cc3666

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07595368B2