2-Chlorobenzenesulfonyl chloride → 2-Chlorobenzenesulfonic acid 3-benzyloxyphenyl ester

HRID 482079

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[S:32](Cl)(=[O:34])=[O:33]>C=Cl.C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([O:15][S:32]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[Cl:25])(=[O:34])=[O:33])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3-benzyloxyphenol (2.97 g, 15 mmol), as prepared in the preceding step, in methylene chlorine (50 mL) at 0° C., was added N,N-diisopropylethylamine (2 mL) and 2-chlorobenzenesulfonyl chloride (3.27 g, 15.5 mmol). The reaction mixture was stirred at 0° C. for 2 h and at room temperature for 2 h. The reaction mixture was diluted with methylene chloride (200 mL), washed sequentially with saturated NaHCO3 (2×50 mL) and brine (2×50 mL), dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography (1:1 hexane:methylene chloride) to give the title compound as a colorless liquid (5.35 g, 95%). 1H-NMR (300 MHz, CDCl3) δ 4.97 (s, 2H), 6.71 (dd, 1H), 6.78 (t, 1H), 6.85 (dd, 1H), 7.17 (t, 1H), 7.37 (m, 5H) 7.58 (m, 2H), 7.91 (dd, 1H).

Workup

washwashed sequentially with saturated NaHCO3 (2×50 mL) and brine (2×50 mL)
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by flash column chromatography (1:1 hexane:methylene chloride)

Sources & evidence

ORD record: ord-5c3bcc26d948446b9669f45c51ee5114
Source dataset: uspto-grants-1998_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05792769

Linked notes

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