Hydrochloric Acid → 2,6-Dichloro-4-hydroxybenzaldehyde

Participants

Reaction Steps

To a 500 mL rbf at −78° C. was added 80 mL THF, 15.5054 g (55.9 mmol) of 4-(tert-Butyl-dimethyl-silanyloxy)-2,6-dichloro-benzaldehyde, stirred 10 min. Then added 41.1423 mL (57.6 mmol) of sec-butyllithium drop-wise over 25 min, and allowed to stir at −78° C. for 1.5 h. To the mostly yellow suspension was added 6.4682 mL (83.9 mmol) of DMF. The yellow solution was allowed to stir at −78° C. for 5 h. To the reaction mixture was added 1 mL MeOH, and 60 mL of 1 N HCl and allowed to warm to r.t. for 18 h. The brown solution was brought to pH 4, extracted with EtOAc, washed with water, brine, and dried with Na2SO4. Solid drop out of organic, filtered and rinsed with DCM to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 6.93 (s, 2H) 10.24 (s, 1H) 11.45 (s, 1H). MS (m/z) 191.0 M (+1), tR=1.07, Meth 10

Provenance & Evidence