Sulfuryl chloride → HCID 58934907, compound

HRID 855025Notes

Reaction equation

HRID 855025 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[OH:13])[O:9][CH:8]([C:14]([F:17])([F:16])[F:15])[C:7]([C:18]([OH:20])=[O:19])=[CH:6]2)[CH3:2].S(Cl)([Cl:24])(=O)=O>ClCCl>[Cl:24][C:4]1[C:3]([CH2:1][CH3:2])=[C:12]([OH:13])[CH:11]=[C:10]2[C:5]=1[CH:6]=[C:7]([C:18]([OH:20])=[O:19])[CH:8]([C:14]([F:15])([F:16])[F:17])[O:9]2

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 58934586HCID 58934586, compound

Product 1

HCID 58934907HCID 58934907, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 100 mg (0.35 mmol) of 6-ethyl-7-hydroxy-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid in 5 mL of anhydrous dichloromethane was added dropwise a solution of 0.42 mL (1.0 M in dichloromethane, 0.42 mmol) sulfuryl chloride. The resulting solution was stirred at room temperature for one hour. The sample was concd and the residue purified on a silica gel column with ethyl acetate:hexane: acetic acid to give 60 mg (52%) of a light yellow solid: 1H NMR(CDCl3/400 MHz) 7.71(s, 1H), 6.71(s, 1H), 5.99(s, 1H), 5.65(q, J=6.0 Hz, 1H), 2.38(m, 1H), 2.06(m, 1H), 0.84(t, J=7.6 Hz, 3H); MS (ESI+) 323.0 (M+1, 100); LCMS (ES−) 321 (M−H, 100); HRMS (ES−) m/z calcd for (M−1; C13H9ClF3O4) 321.0136, found 321.0118.

Workup

  1. customthe residue purified on a silica gel column with ethyl acetate

Sources & evidence

ORD record
ord-0ebf07a0cf94459c889931a9aa900441
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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