Hydrochloric Acid → HCID 60167283, compound

Participants

Reaction Conditions

Reaction Steps

Ester 8 (2.29 g, 5.94 mmol) was dissolved in a 3:1:1 mixture of THF:CH3OH:H2O (0.1 M). LiOH—H2O was added and the reaction mixture was stirred at 25° C. for 24 h. Upon completion, the reaction mixture was acidified to pH 1 with the addition of 10% aqueous HCl. A precipitate formed during the acidification and it was collected by vacuum filtration. The remaining aqueous layer was then extracted with ethyl acetate (3×). The organic extracts were combined, dried over Na2SO4, and concentrated under reduced pressure. The filtered and extracted products were combined to give 9 (2.09 g, 100%) as a pale yellow solid. 1H NMR (DMSO-d6, 500 MHz) δ 8.23 (s, 1H), 8.10 (d, J=6.0 Hz, 1H), 7.91 (d, J=6.5 Hz, 1H), 7.61 (d, J=7.0 Hz, 2H), 7.55 (s, 1H), 7.43-7.39 (m, 3H), 7.33 (t, J=7.0 Hz, 1H), 5.35 (s, 2H). 13C NMR (DMSO-d6, 125 MHz) δ 166.7, 153.8, 136.2, 135.9, 135.0, 129.8, 128.8, 128.2, 127.8, 127.7, 127.5, 124.7, 123.8, 115.5, 107.0, 70.4. IR (film) νmax 3368, 2969, 1680 cm−1. ESI-TOF HRMS m/z 357.0125 (M+H+, C18H13BrO3 requires 357.0121).

Provenance & Evidence