Acetonitrile → HCID 71696927, compound

HRID 1498987Notes

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-:25])[O-:24].[C:27](#N)[CH3:28].[CH3:30][CH2:31]OC(C)=O>>[F:14][C:10]1[CH:9]=[C:8]([P:23](=[O:26])([O:25][CH2:27][CH3:28])[O:24][CH2:30][CH3:31])[CH:7]=[CH:12][C:11]=1[F:13]

Participants

Reactant 5

HCID 6342Acetonitrile

HCID 8857Ethyl Acetate

HCID 25953Cesium fluoride

HCID 107908Phosphite

HCID 10860596HCID 10860596, compound

Product 1

HCID 71696927HCID 71696927, compound

Procedure

4,5-difluoro-2-(trimethylsilyl)phenyl trifluoromethanesulfonate (25 mg, 0.078 mmol), Cesium Fluoride (62 mg, 0.411 mmol), Triethtyl phosphite (50 mg, 0.299 mmol), Acetonitrile (1 ml): Reaction Time 4 h; Rf: 0.5 (2:3 EtOAc:Pet Ether); Thick oil; 14.6 mg, 78%; 1H NMR (500 MHz, CDCl3, TMS) δ 7.67-7.55 (m, 2H), 7.31-7.23 (m, 1H), 4.21-4.05 (m, 4H), 1.34 (t, J=7.0 Hz, 6H); 13C NMR (125 MHz, CDCl3, TMS) δ 153.1 (ddd, J=3.8, 12.4, 255.6 Hz), 150.2 (ddd, J=13.4, 22.9, 252.7 Hz), 128.8 (ddd, J=3.8, 6.7, 10.5 Hz), 125.9 (dt, J=3.8, 192.7 Hz), 121.1 (dd, J=11.4, 18.1 Hz), 117.9 (t, J=18.1 Hz), 62.4 (d, J=4.8 Hz), 16.2 (d, J=5.7 Hz) 31P NMR (162 MHz, CDCl3) δ 15.8 (apparent t, JPF=6.1 Hz); HRMS-ESI (m/z) calcd (C10H13F2O3P+H)+: 251.0643. found: 251.0643.

Sources & evidence

ORD record: ord-775dd2a4d41449e8989d98f19b37d01f
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09200018B2

Reaction notes

Loading…