Chlorosulfonic acid → [2-(2-Benzenesulfonyl-ethoxycarbonylmethoxy)-4-chlorosulfonyl-phenoxy]-acetic acid 2-benzenesulfonyl-ethyl ester

HRID 2182863Notes

Reaction equation

[C:1]1([S:7]([CH2:10][CH2:11][O:12][C:13](=[O:38])[CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH2:23][C:24]([O:26][CH2:27][CH2:28][S:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)(=[O:31])=[O:30])=[O:25])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:39][S:40](O)(=[O:42])=[O:41]>C(Cl)Cl>[C:1]1([S:7]([CH2:10][CH2:11][O:12][C:13](=[O:38])[CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([S:40]([Cl:39])(=[O:42])=[O:41])=[CH:18][C:17]=2[O:22][CH2:23][C:24]([O:26][CH2:27][CH2:28][S:29]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)(=[O:31])=[O:30])=[O:25])(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of [2-(2-benzenesulfonyl-ethoxycarbonylmethoxy)phenoxy]acetic acid 2-benzenesulfonyl-ethyl ester (Intermediate 28, 7.4 g, 13.2 mmol) in 10 mL of CH2Cl2 was added drop-wise ClSO3H (5.0 mL, 8.8 g, 75.8 mmol, 5.7 eq) at 0° C. with vigorous stirring. The mixture was stirred at 0° C. for 1.5 h. and then poured onto crushed ice with vigorous stirring, resulting in a thick mass. This was extracted with CH2Cl2. The organic layers were dried and concentrated under reduced pressure. The residual oil was dried under vacuum overnight to give Intermediate 29 (8.0 g, 92%) as an off-white foam.

Workup

additionpoured
customonto crushed ice with vigorous stirring
customresulting in a thick mass
extractionThis was extracted with CH2Cl2
customThe organic layers were dried
concentrationconcentrated under reduced pressure
customThe residual oil was dried under vacuum overnight

Sources & evidence

ORD record: ord-956ef8f0a63f4eadb0c3a5797ef840b9
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06897227B2

Reaction notes

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