Chlorodifluoromethane → HCID 66752947, compound

HRID 1642391Notes

Reaction equation

HRID 1642391 reaction equation
C([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:15](=[O:16])[N:14]3[CH:17]=[CH:18][S:19][C:13]3=[N:12][C:11]=2[CH3:20])=[CH:6][CH:5]=1)C.C([O-])([O-])=O.[Cs+].[Cs+].Cl[CH:28]([F:30])[F:29]>CN(C=O)C.C(OCC)(=O)C>[F:29][CH:28]([F:30])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:15](=[O:16])[N:14]3[CH:17]=[CH:18][S:19][C:13]3=[N:12][C:11]=2[CH3:20])=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 6372ChlorodifluoromethaneHCID 10796Cesium carbonateHCID 66753310HCID 66753310, compound

Product 1

HCID 66752947HCID 66752947, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Step 1 intermediate, Intermediate 10 (400 mg, 1.548 mmol) in DMF (15 ml) was treated with Cs2CO3 (1.513 g, 4.645 mmol) slowly at room temperature. The reaction temperature was raised to 80° C. at which the chloro-difluoro-methane (ClCHF2) gas was passed into the reaction mixture till TLC indicated completion of the reaction. The reaction mixture was diluted with ethyl acetate, washed with water and brine, dried over anhydrous Na2SO4 and purified using column chromatography to afford the desired compound; 1H NMR (300 MHz, CDCl3) δ 2.20 (s, 3H), 7.18-7.22 (m, 2H), 7.25 (s, 1H), 7.37-7.40 (m, 2H), 7.55 (d, J=5.1 Hz, 1H), 7.99 (d, J=4.8 Hz, 1H); ESI-MS (m/z) 309.45 (M+H)+.

Workup

  1. customcompletion of the reaction
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. custompurified

Sources & evidence

ORD record
ord-833423b2e9f54bf5b9aae54e96b9472e
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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