Acetonitrile → HCID 118260394, compound

HRID 1498988Notes

Reaction equation

HRID 1498988 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[C:11]([F:13])[C:10]([F:14])=[CH:9][C:8]=1[Si](C)(C)C)(=O)=O.[F-].[Cs+].[P:23]([O-:26])([O-])[O-:24].[C:27](#N)C.CCO[C:33](C)=[O:34]>>[F:14][C:10]1[CH:9]=[C:8]([P:23](=[O:26])([O:34][CH3:33])[O:24][CH3:27])[CH:7]=[CH:12][C:11]=1[F:13]

Participants

6

Reactant 5

HCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 25953Cesium fluorideHCID 107908PhosphiteHCID 10860596HCID 10860596, compound

Product 1

HCID 118260394HCID 118260394, compound

Procedure

4,5-difluoro-2-(trimethylsilyl)phenyl trifluoromethanesulfonate (25 mg, 0.074 mmol), Cesium Fluoride (62 mg, 0.411 mmol), Trimethtyl phosphite (37 mg, 0.299 mmol), Acetonitrile (1 ml): Reaction Time: 4 h; Rf: 0.4 (1:3 EtOAc:Pet Ether); Thick oil; 11.8 mg, 71%; 1H NMR (400 MHz, CDCl3, TMS) δ 7.67-7.53 (m, 2H), 7.34-7.24 (m, 1H), 3.79 (s, 3H), 3.77 (s, 3H); 13C NMR (100 MHz, CDCl3, TMS) δ 153.3 (ddd, J=3.9, 12.3, 256.6 Hz), 150.3 (ddd, J=12.3, 22.4, 252.0 Hz), 129.0 (ddd, J=3.9, 6.9, 10.8 Hz), 124.2 (dt, J=3.9, 193.4 Hz), 121.3 (dd, J=11.6, J=18.5 Hz), 118.0 (t, J=17.7 Hz), 52.9 (d, J=6.2 Hz); 31P NMR (162 MHz, CDCl3) δ 18.6 (d, JPF=7.5 Hz); HRMS-ESI (m/z) calcd (C8H9F2O3P+H)+: 223.0330. found: 223.0335.

Workup

  1. custom4 h

Sources & evidence

ORD record
ord-d4c78f1d98ba46e98a2287ee3de0520c
Source dataset
uspto-grants-2015_12
Patent number
US09200018B2

Reaction notes

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