Water → 3-Hydroxy-4-hydroxymethylbenzamide

Reaction equation

[O:1]([C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[CH2:18]Br)[C:12]([NH2:14])=[O:13])[Si](C(C)(C)C)(C)C.[OH2:20]>CC#N.[F-].[K+]>[OH:1][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[CH2:18][OH:20])[C:12]([NH2:14])=[O:13]

Participants

Procedure

To the solution of 3-t-butyldimethylsiloxy-4-bromomethylbenzamide (Compound 7.2) (0.101 g, 0.293, mmol) in 8 mL CH3CN, KF.2H2O (0.041 g, 0.44 mmol) in 4 mL H2O was added dropwise. The mixture was then stirred at room temperature for half hour. After the solvent was removed, the residue was absorbed on 500 mg silica gel. The product was obtained by flash chromatography (ethyl acetate:ethyl alcohol=10:1, Rf=0.8) as a white solid (0.0439 g, y==90.7%). 1H NMR (CD3CN) δ4.68(s,2H), 5.95(b,1H), 6.69(b,1H), 7.23-7.26(m,3H), 7.77(b,1H); 13C NMR (CD3Cl) δ60.66, 115.13, 119.44, 128.69, 133.07, 134.94, 156.10, 203.64.