2-Methyl-2-butene → HCID 73554900, compound

To a solution of 4-bromo-2-fluoro-6-methoxy-benzaldehyde (3.4 g, 14.6 mmol) in tert-butanol (70 ml) and water (35 ml), sodium chlorite (2.64 g, 29.2 mmol), monosodium phosphate dihydrate (11.4 g, 72.9 mmol) and 2-methyl-2-butene (12.4 ml, 116.7 mmol) are added successively at room temperature and the mixture is stirred for 2 h. After completion of the reaction (monitored by TLC), the mixture is concentrated under reduced pressure and the residue is diluted with ice water (50 ml) and acidified to pH 5 by adding 2N hydrochloric acid. The mixture is extracted with methyl tert-butyl ether (2×100 ml). The methyl tert-butyl ether layer is extracted again with 10% aqueous sodium hydroxide (100 ml). The aqueous layer is acidified to pH 2 with 5N hydrochloric acid and extracted with dichloromethane (2×50 ml). The organic layer is washed with brine (50 ml), dried over sodium sulfate and evaporated to dryness to obtain 4-bromo-2-fluoro-6-methoxy-benzoic acid (2.5 g, 10.0 mmol, 68%).

1. customAfter completion of the reaction (monitored by TLC)
2. concentrationthe mixture is concentrated under reduced pressure
3. additionthe residue is diluted with ice water (50 ml)
4. additionby adding 2N hydrochloric acid
5. extractionThe mixture is extracted with methyl tert-butyl ether (2×100 ml)
6. extractionThe methyl tert-butyl ether layer is extracted again with 10% aqueous sodium hydroxide (100 ml)
7. extractionextracted with dichloromethane (2×50 ml)
8. washThe organic layer is washed with brine (50 ml)
9. dry with materialdried over sodium sulfate
10. customevaporated to dryness

ORD record

ord-141a444dfcb04cb3b19b0e706d7b3311

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09108936B2