Triphenylphosphine → HCID 68558983, compound

HRID 2036131Notes

Reaction equation

HRID 2036131 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]=[C:10]([CH2:13][OH:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][C:17]=1O.CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH2:1]([N:8]1[CH2:12][CH:11]=[C:10]([CH2:13][O:14][C:17]2[CH:18]=[C:19]([C:22]([F:24])([F:25])[F:23])[CH:20]=[CH:21][C:16]=2[Br:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 14667724HCID 14667724, compoundHCID 219144702-Bromo-5-(trifluoromethyl)phenol

Product 1

HCID 68558983HCID 68558983, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

(1-Benzyl-2,5-dihydro-1H-pyrrol-3-yl)methanol (11.44 g) obtained in Example 50(2), 2-bromo-5-trifluoromethylphenol (16.04 g), DEAD (40% toluene solution, 11.06 mL) and triphenylphosphine (18.95 g) were dissolved in tetrahydrofuran (450 mL). The reaction solution was stirred at 50° C. overnight. Tetrahydrofuran was evaporated under reduced pressure, and the residue was purified by silica gel column (10% ethyl acetate/petroleum ether to 20% ethyl acetate/petroleum ether) to give the object product as a white solid (12.3 g, 49%).

Workup

  1. customTetrahydrofuran was evaporated under reduced pressure
  2. customthe residue was purified by silica gel column (10% ethyl acetate/petroleum ether to 20% ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-01779bffd52e440ab2cee18363626cd8
Source dataset
uspto-grants-2013_11
Patent number
US08575167B2

Reaction notes

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