Hydrochloric Acid → HCID 57443330, compound

The mixture of 2-bromo-4-methyl-benzoic acid (9.5 g, 32.3 mmol), THF (30.0 mL), and 5.0 M NaOH (26 mL, 129 mmol) is stirred at room temperature overnight. The mixture is acidified with 5.0 M HCl and is extracted with EtOAc (80 mL). The organic phase is washed with brine (60 mL) and is dried (Na2SO4). After filtration, the filtrate is concentrated under reduced pressure to a residue. The residue is dissolved in CH2Cl2 (50 mL) and MeOH (50 mL) and is treated with 2.0 M TMSCHN2 in hexane (30 mL, 60 mmol) at 0° C. for 1.0 h. The reaction mixture is concentrated to a residue and the residue is purified by flash chromatography to afford the title compound as a solid (2.3 g, 29%). LC-ES/MS m/e 247.0 (M+1).

1. extractionis extracted with EtOAc (80 mL)
2. washThe organic phase is washed with brine (60 mL)
3. dry with materialis dried (Na2SO4)
4. filtrationAfter filtration
5. concentrationthe filtrate is concentrated under reduced pressure to a residue
6. dissolutionThe residue is dissolved in CH2Cl2 (50 mL)
7. concentrationThe reaction mixture is concentrated to a residue
8. customthe residue is purified by flash chromatography

ORD record

ord-e04ac2b338534d49b1a052ad89672a93

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07846960B2