Dimethylformamide → HCID 86723698, compound

Temperature

0 °C

To a 0° C. solution of 6-bromo-2-methyl-3-(propan-2-yloxy)benzoic acid (Cpd OO, 1.30 g, 4.80 mmol) in DCM (5 mL) was added oxalyl chloride (810 mg, 6.19 mmol) followed by DMF (10 mL). The reaction mixture was stirred at 0° C. for 1.5 hours, then concentrated under vacuum. The residue was dissolved in MeOH (15 mL) and stirred at room temperature for 1.5 hours. The reaction mixture was concentrated under vacuum and the residue dissolved in EtOAc. The organic layer was washed with brine, dried with Na2SO4, and concentrated under vacuum. The residue was purified by column chromatography (0-50%, EtOAc/heptane) to give the title compound (Cpd PP, 894 mg, 65%) as an amber oil. 1H NMR (400 MHz, chloroform-d) δ 1.33 (d, J=6.11 Hz, 6H) 2.16 (s, 3H) 3.95 (s, 3H) 4.50 (dt, J=12.04, 6.08 Hz, 1H) 6.75 (d, J=8.80 Hz, 1H) 7.31 (d, J=8.80 Hz, 1H); MS 287 [M+H].

1. concentrationconcentrated under vacuum
2. dissolutionThe residue was dissolved in MeOH (15 mL)
3. stirringstirred at room temperature for 1.5 hours
4. concentrationThe reaction mixture was concentrated under vacuum
5. dissolutionthe residue dissolved in EtOAc
6. washThe organic layer was washed with brine
7. dry with materialdried with Na2SO4
8. concentrationconcentrated under vacuum
9. customThe residue was purified by column chromatography (0-50%, EtOAc/heptane)

ORD record

ord-f199349f669f4febb51ae3b8bf876a3b

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09040515B2