Chlorosulfonic acid → HCID 21883492, compound

HRID 2297869Notes

Reaction equation

[Cl:1][S:2]([OH:5])(=O)=[O:3].[F:6][C:7]([F:22])([F:21])[CH:8]1[C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]2[CH:17]=[CH:18][CH:19]=[CH:20][C:10]=2[O:9]1>C(OCC)C>[Cl:1][S:2]([C:18]1[CH:19]=[CH:20][C:10]2[O:9][CH:8]([C:7]([F:22])([F:21])[F:6])[C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]=2[CH:17]=1)(=[O:5])=[O:3]

Participants

Conditions

Temperature: -15 °C

Procedure

To chlorosulfonic acid (50.0 mL) chilled to −15° C. was added 2-(trifluoromethyl)-2H-1-benzopyran-3-carboxylic acid (Example 10) (4.0 g, 16.7 mmol). After stirring at −15° C. for 1 hour, the solution was warmed to room temperature and stirred for 16 hours. The resulting solution was added dropwise over ice (100 mL) with two diethyl ether(2×75 mL) extractions. The diethyl ether layers were combined, washed with water (2×75 mL), and brine (2×75 mL, dried over sodium sulfate and concentrated in vacuo. The resulting solids were triturated with hexane-ethyl acetate (9:1, 100 mL). The 6-chlorosulfonyl-2-trifluoromethyl-2H-1-benzopyran-3-carboxylic acid was isolated as a white solid: mp 169-174. 1H NMR (CD3OD/300 MHz) 8.18 (d, 1H, J=2.7 Hz), 8.06 (dd, 1H, J=8.7, 2.7 Hz), 7.93 (s, 1H), 7.28 (d, 1H, J=8.7 Hz), 6.00 (q, 1H, J=6.6 Hz). EIHRMS m/z 324.9977 (M+, Calcd 324.9994).

Workup

temperaturethe solution was warmed to room temperature
stirringstirred for 16 hours
washwashed with water (2×75 mL), and brine (2×75 mL
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customThe resulting solids were triturated with hexane-ethyl acetate (9:1, 100 mL)

Sources & evidence

ORD record: ord-8821aacbe707457e95d39cd08c373b0f
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492390B2

Reaction notes

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