Potassium Phosphate, Tribasic → HCID 18451502, compound

Temperature

95 °C

A mixture of 2-chloro-4-bromo-5-methyl-3,6-difluoroaniline (7.0 g, 27 mmol) cyclopropylboronic acid (3.5 g, 41 mmol), palladium(II) acetate (0.67 g, 3.0 mmol), potassium phosphate (17.5 g, 82 mmol) and tricyclohexylphosphine (0.83 g, 3.0 mmol) is dissolved in 100 mL of 4:1 toluene/water. The mixture is degassed by repeated alternating applications of vacuum and positive nitrogen pressure (10×). The mixture is heated to 95° C. for 2 days and then cooled to room temperature. Most of the toluene is removed by rotary evaporator and the residual mixture is partitioned between Et2O (250 mL) and water (250 mL). The organic phase is washed with brine (3×250 mL), dried (MgSO4) and concentrated by rotary evaporator. The crude product is purified using flash chromatography (10% EtOAc/hexanes) to give 2-chloro-4-cyclopropyl-5-methyl-3,6-difluoroaniline as a tan oil.

1. customThe mixture is degassed
2. temperaturecooled to room temperature
3. customMost of the toluene is removed by rotary evaporator
4. customthe residual mixture is partitioned between Et2O (250 mL) and water (250 mL)
5. washThe organic phase is washed with brine (3×250 mL)
6. dry with materialdried (MgSO4)
7. concentrationconcentrated by rotary evaporator
8. customThe crude product is purified

ORD record

ord-e664f320bf8b47ddb4410e967c646bd6

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07202364B2