Triphenylphosphine → HCID 66649725, compound

HRID 420333Notes

Reaction equation

HRID 420333 reaction equation
[C:1]([C:5]1[CH:6]=[C:7](OS(C(F)(F)F)(=O)=O)[CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC)(C)C.C[C:47]([N:49](C)C)=O>[C-]#N.[C-]#N.[Zn+2].CC([O-])=O.CC([O-])=O.[Pd+2]>[C:1]([C:5]1[CH:6]=[C:7]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[C:47]#[N:49])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 15413tert-Butyl methyl etherHCID 31374DimethylacetamideHCID 86639551HCID 86639551, compound

Product 1

HCID 66649725HCID 66649725, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
150 °C

Procedure

A mixture of trifluoro-methanesulfonic acid 3-tert-butyl-5-methoxy-phenyl ester (60.67 g, 194 mmol), Zn(CN)2 (15.97 g, 136 mmol), PPh3 (8.15 g, 31.1 mmol) and Pd(OAc)2 (1.745 g, 7.77 mmol) in dimethyl acetamide (174 mL) was heated at 150° C. for 16 h. The cold reaction mixture was poured onto water and TBME. The mixture was filtered over Celite, separated and the organic phase was washed with 1M H2SO4, water and brine. The product was dried over MgSO4, evaporated and distilled at ˜5 mbar, bp 94-100° C. to provide the title compound as a colorless oil: TLC (AcOEt-hexane 1:9) Rf=0.35; LCMS RtH2=2.73 min; ESIMS [M+H]+=190; 1H NMR (400 MHz, CDCl3): δ 7.27 (s, 1H), 7.13 (s, 1H), 6.93 (s, 1H), 3.82 (s, 3H), 1.30 (s, 9H).

Workup

  1. customThe cold reaction mixture
  2. filtrationThe mixture was filtered over Celite
  3. customseparated
  4. washthe organic phase was washed with 1M H2SO4, water and brine
  5. dry with materialThe product was dried over MgSO4
  6. customevaporated
  7. distillationdistilled at ˜5 mbar, bp 94-100° C.

Sources & evidence

ORD record
ord-03528ba9b3e24cc99f6e1087651db273
Source dataset
uspto-grants-2012_01
Patent number
US08093406B2

Reaction notes

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