3-Bromo-2-methoxybenzoic acid → 3-Bromo-2-methoxybenzenemethanol

Temperature

0 °C

In a 250 ml round bottom flask, 3-bromo-2-methoxybenzoic acid (4.0 g, 17 mmol, 1.0 eq) was dissolved in THF (100 mL). The solution was cooled to 0° C. To above solution was added dropwise borane/THF complex (1 N, 17.3 mL, 17.3 mmol). The solution was warmed to r.t. and let stirred at r.t for 15 hr. The reaction was quenched with addition of aqueous ammonium chloride and concentrated. The mixture was diluted with EtOAc, washed with 1 N HCl followed by aqueous sodium bicarbonate solution, brine and water. The organic phase was dried over MgSO4, filtered and concentrated. The crude product was used without purification.

1. additionTo above solution was added dropwise borane/THF complex (1 N, 17.3 mL, 17.3 mmol)
2. temperatureThe solution was warmed to r.t.
3. customThe reaction was quenched with addition of aqueous ammonium chloride
4. concentrationconcentrated
5. additionThe mixture was diluted with EtOAc
6. washwashed with 1 N HCl
7. dry with materialThe organic phase was dried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated
10. customThe crude product was used without purification

ORD record

ord-655a51c203f048c39d5277afa11c6af3

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09018211B2