Dichloromethane → HCID 86700905, compound

Temperature

-78 °C

A stirred solution of 4-chloro-2,6-dimethoxybenzaldehyde (Example 37A, 1.95 g, 9.72 mmol) in DCM (20 mL, 311 mmol) at −78° C. was slowly added boron tribromide (9.72 mL, 9.72 mmol). The reaction mixture was stirred at −78° C. for 10 minutes then warmed to r.t. and stirred for 1 hour while monitoring reaction progress by LCMS. Once all s.m. had been consumed, the reaction was quenched with water and extracted with DCM. The organic phase was washed with brine, dried (MgSO4), filtered and concentrated to dryness to give the title material (1.79 g, 9.59 mmol, 99% yield) as a purple solid. LC (Method B): 2.199 min. LCMS (APCI) calcd for C8H8ClO3 [M+H]+ m/z 187.02, found 187.0. 1H NMR (CDCl3, 400 MHz) δ ppm: 11.89 (s, 1H), 10.20 (s, 1H), 6.75 (t, J=2.0 Hz, 1H), 6.66 (m, 1H), 3.91 (s, 1H).

1. customat −78° C.
2. temperaturethen warmed to r.t.
3. stirringstirred for 1 hour
4. customreaction progress by LCMS
5. customhad been consumed
6. customthe reaction was quenched with water
7. extractionextracted with DCM
8. washThe organic phase was washed with brine
9. dry with materialdried (MgSO4)
10. filtrationfiltered
11. concentrationconcentrated to dryness

ORD record

ord-813a75e4add842199c8a3735eb80a421

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09303065B2