5-chloro-2,4-dihydroxybenzaldehyde

To a solution of 2, 4-dihydroxybenzaldehyde (3.0 g, 22 mmol) in Et20 (100 mL, 0.22 M) was added dropwise sulfurylchloride (2.1 mL, 26 mmol) at 0 °C under argon. After being stirred at RT for 30 min, the reaction solution was poured into ice-chilled brine, washed with H2O and brine, dried over MgS04, filtered, and concentrated. Purification by flash chromatography (Et20:hexanes = 1:2) provided compound 6 as an ivory solid (47percent). NMR (DMSO-d6, 300 MHz): δ 11.38 (1H, s), 10.87 (1H, s), 9.97 (1H, s), 7.59 (1H, s), 6.58 (1H, s). LRMS (APCI+): Calc'd for C7H5C103 172.0 m/z, measured 173.1 (MH+).To a solution of2, 4-dihydroxybenzaldehyde (3.0 g, 22 mmol) in Et20 (100 mE, 0.22 M) was added dropwise sulfurylchloride (2.1 mE, 26 mmol) at 00 C. under argon. Afier being stirred at RT for 30 mm, the reaction solution was poured into ice-chilled brine, washed with H20 and brine, dried over MgSO4, filtered, and concentrated. Purification by flash chromatography (Et20:hexanes=1 :2) provided compound 6 as an ivory solid (47percent). ‘H NMR (DMSO-d6, 300 MHz): ö 11.38 (1H, s), 10.87 (1H, s), 9.97 (1H, s), 7.59 (1H, s), 6.58 (1H, s). ERMS (APCI+): Calc’d for C7H5C10C3 172.0 ink, measured 173.1 (MH+).To a solution of 2, 4-dihydroxybenzaldehyde (20 g, 144.92 mmol) in diethyl ether (500 mL) was added drop wise sulfuryl chloride (14 mL, 171.2 mmol) at 0° C. under argon and stirred at room temperature for 30 min. The reaction mixture was poured into ice-water, the organic layer was separated and washed with water, brine, dried over NaSodium hypochlorite (75 mL, 0.055 mol) and piperidine (4.68 g, 0.055 mol) were cooled to 0° C., combined cautiously and added dropwise over 2 h to a solution of 2, 4, -dihydroxybenzaldehyde (6.91 g, 0.05 mol) in 50percent aqueous sulfuric acid (150 mL) while cooling to 0° C.In a scintillation vial, 2, 4-dihydroxybenzaldehyde (1.38 g, 10 mmol) was dissolved in ethyl ether (18 ml). The mixture was placed under N2 atmosphere and cooled to 0° C. To the mixture was added sulfuryl chloride (0.91 ml, 11 mmol). The mixture was kept under N2 atmosphere at 0° C. for 30 minutes. The reaction mixture was poured into ice water and extracted with ethyl acetate (20 ml). Organic layer was washed with brine, concentrated and chromatographed to yield 5-chloro-2, 4-dihydroxybenzaldehyde (0.55 g, 3.2 mmol, 32percent) and 3-chloro-2, 4-dihydroxybenzaldehyde (0.233 g, 1.34 mmol, 13.4percent)

Molecular Weight:172.56
XLogP3:1.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:171.9927217
Monoisotopic Mass:171.9927217
Topological Polar Surface Area:57.5
Heavy Atom Count:11
Complexity:151
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes