Dichloromethane → HCID 58934931, compound

HRID 855026Notes

Reaction equation

HRID 855026 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:10](=C[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.Cl[CH2:27][Cl:28]>C(OCC)(=O)C>[Cl:24][C:4]1[C:3]([CH2:1][CH3:2])=[C:12]([OH:13])[C:27]([Cl:28])=[C:10]2[C:5]=1[CH:6]=[C:7]([C:18]([OH:20])=[O:19])[CH:8]([C:14]([F:17])([F:16])[F:15])[O:9]2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24648Sulfuryl chlorideHCID 58934586HCID 58934586, compound

Product 1

HCID 58934931HCID 58934931, compoundYield 21.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 1.5 g (5.2 mmol) of 6-ethyl-7-hydroxy-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid in 45 mL of anhydrous dichloromethane was added dropwise a solution of 1.0 M sulfuryl chloride (22.75 mmol, 4.4 eqv). The resulting suspension was stirred at room temperature for 12 h; the reaction turned into a clear yellow solution. The sample was concd and the residue dissolved in ethyl acetate, washed with brine and dried over anhydrous magnesium sulfate. Silica chromatography with ethyl acetate:hexane:acetic acid as the eluant afforded 0.12 g (21.5%) of a white solid: 1H NMR (CDCl3/400 MHz) 7.72(s, 1H), 6.68(s, 1H), 5.79(q, J=5.6 Hz, 1H), 2.42(m, 1H), 2.11(m, 1H), 0.85(t, J=7.6 Hz, 3H). MS (ESI+) 357.0 (M+1, 100). MS(ES−) 355.0 (M−H, 100). HRMS (ES−) m/z calcd for (C13H8Cl2F3O4) M−H: 354.9746, found: 354.9724.

Workup

  1. washwashed with brine
  2. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-16191e27b50140c782ac7a374ad85b08
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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