Nanofin → HCID 67537407, compound

HRID 2240985Notes

Reaction equation

HRID 2240985 reaction equation
[CH2:1]([O:3][P:4]([CH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12](Br)[CH:11]=1)[F:9])[O:5][CH2:6][CH3:7])[CH3:2].CC1CCCC(C)N1.[F:25][CH:26]([F:36])[O:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]#[CH:35])=[CH:30][CH:29]=1>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH2:1]([O:3][P:4]([CH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:35]#[C:34][C:31]2[CH:30]=[CH:29][C:28]([O:27][CH:26]([F:25])[F:36])=[CH:33][CH:32]=2)[CH:11]=1)[F:9])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

6

Reactant 3

HCID 68843NanofinHCID 27784971-(Difluoromethoxy)-4-ethynylbenzeneHCID 67539254HCID 67539254, compound

Product 1

HCID 67537407HCID 67537407, compoundYield 53.4%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of diethyl[(3-bromophenyl)(fluoro)methyl]phosphonite (5.5 g, 17.0 mmol), 2,6-dimethylpiperidine (10 mL), and 1-(difluoromethoxy)-4-ethynylbenzene (3.38 g, 20.4 mmol) was degassed with argon for 5 minutes. Then, tetrakis(triphenylphosphine) palladium (0) (983 mg, 0.85 mmol) was added and the mixture was stirred at 80° C. for 5 hours. The mixture was poured into water and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and purification by ICSO (hexane/EtOAc 1/1) gave diethyl[(3-{[4-(difluoromethoxy)phenyl]ethynyl}phenyl)(fluoro)methyl]phosphonite (3.6 g) as a clear oil; MS m/e (M+H)+ 413.

Workup

  1. customwas degassed with argon for 5 minutes
  2. extractionextracted with EtOAc
  3. dry with materialThe organic extracts were dried over MgSO4
  4. customEvaporation and purification by ICSO (hexane/EtOAc 1/1)

Sources & evidence

ORD record
ord-266bc708f4fb44749b0c5617926f178c
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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