4-Bromo-1-[(2,2-dimethoxyethyl)oxy]-2-methylbenzene → 5-Bromo-7-methylbenzofuran

Polyphosphoric acid (2.0 g) was added to a solution of 4-bromo-1-[(2,2-dimethyloxyethyl)oxy]-2-methylbenzene (6.24 g) in toluene (100 ml) and the resulting mixture was warmed to reflux for 4 hours. The reaction mixture was cooled to room temperature and the supernatant organic layer decanted off. The black residue was basified with 2N aqueous Na2CO3 and extracted with ethyl acetate (100 ml). The organic layers were combined, washed with brine (2×100 ml), dried over MgSO4, ifitered, and the solvent removed under reduced pressure. Purification by MPLC (2% ethyl acetatein-hexane) gave 5-bromo-7-methyl-benzofaran as a colourless oil (2.77 g). 1H NMR (360 MHz,CDCl3)δ2.48 (3H, s), 6.68 (1H, d, J=3.6 Hz), 7.13 (1H, s), 7.53 (1H, s), 7.60 (1H, d, J=3.6 Hz).

1. temperaturethe resulting mixture was warmed
2. temperatureto reflux for 4 hours
3. customthe supernatant organic layer decanted off
4. extractionextracted with ethyl acetate (100 ml)
5. washwashed with brine (2×100 ml)
6. dry with materialdried over MgSO4
7. customthe solvent removed under reduced pressure
8. customPurification by MPLC (2% ethyl acetatein-hexane)
9. customgave 5-bromo-7-methyl-benzofaran as a colourless oil (2.77 g)

ORD record

ord-01354a9d5ecc4e08ab5c24dccec4f4b4

Source dataset

uspto-grants-1999_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05985896