Triphenylphosphine → HCID 68557049, compound

HRID 2036130Notes

Reaction equation

HRID 2036130 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]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[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]=[CH:19][C:20]([C:22]([F:25])([F:24])[F:23])=[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 27611682-Bromo-4-(trifluoromethyl)phenolHCID 5462977Diethyl azodicarboxylateHCID 14667724HCID 14667724, compound

Product 1

HCID 68557049HCID 68557049, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

(1-Benzyl-2,5-dihydro-1H-pyrrol-3-yl)methanol (14.0 g) obtained in Example 50(2), 2-bromo-4-trifluoromethylphenol (19.0 g), DEAD (13.5 g) and triphenylphosphine (23.3 g) were dissolved in tetrahydrofuran (450 mL). The reaction solution was stirred under a nitrogen atmosphere at 50° C. overnight. Tetrahydrofuran was evaporated under reduced pressure, and the residue was purified by silica gel column (20% diethyl ether/petroleum ether to 33% diethyl ether/petroleum ether) to give the object product as a pale-yellow oil (10 g, 33%).

Workup

  1. customTetrahydrofuran was evaporated under reduced pressure
  2. customthe residue was purified by silica gel column (20% diethyl ether/petroleum ether to 33% diethyl ether/petroleum ether)

Sources & evidence

ORD record
ord-0c2fedb4d1674d619998532f0d462954
Source dataset
uspto-grants-2013_11
Patent number
US08575167B2

Reaction notes

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