Sulfuryl chloride → HCID 58934712, compound

HRID 855027Notes

Reaction equation

HRID 855027 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.C(O)(=O)C.[Zn]>[Cl:24][C:11]1[C:12]([OH:13])=[C:3]([CH2:1][CH3:2])[CH:4]=[C:5]2[C:10]=1[O:9][CH:8]([C:14]([F:15])([F:16])[F:17])[C:7]([C:18]([OH:20])=[O:19])=[CH:6]2

Participants

6

Reactant 2

HCID 24648Sulfuryl chlorideHCID 58934586HCID 58934586, compound

Product 1

HCID 58934712HCID 58934712, compoundYield 18.2%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1.0 g (3.4 mmol) of 6-ethyl-7-hydroxy-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid in anhydrous dichloromethane (30 mL) was added 4.2 mL (1.0 M in DCM, 22 mmol) sulfuryl chloride dropwise. The resulting mixture was stirred at room temperature for 24 h. The sample was concd and the residue dissolved in 30 mL of acetic acid, followed by addition of 0.5 g granular Zn. The mixture was stirred at room temperature for 3 h, filtered and the filtrate evaporated. The residue was purified by chromatography to afford 0.20 g (18%) of a white solid: 1H NMR(CDCl3/400 MHz) 7.79 (s, 1H), 7.26 (s, 1H), 5.77 (q, J=6.8 Hz, 1H), 2.63(q, J=7.6 Hz, 2H), 1.21(t, J=7.6 Hz, 3H). MS (ESI+) 323.0 (M+1, 100).

Workup

  1. stirringThe mixture was stirred at room temperature for 3 h
  2. filtrationfiltered
  3. customthe filtrate evaporated
  4. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-0a81b0ce193f47a7bbe830f0b72689e6
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

Loading…