Triphenylphosphine → HCID 67384983, compound

HRID 1504301Notes

Reaction equation

HRID 1504301 reaction equation
[Br:1][C:2]1[CH:15]=[C:14]([N+:16]([O-])=O)[C:13]2[C:12]3[C:7](=[CH:8][C:9]([Br:19])=[CH:10][CH:11]=3)[CH2:6][CH2:5][C:4]=2[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClC1C=CC=CC=1Cl>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:5][CH2:6][C:7]3=[CH:8][C:9]([Br:19])=[CH:10][C:11]4[NH:16][C:14]([CH:15]=1)=[C:13]2[C:12]=43

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 67384568HCID 67384568, compound

Product 1

HCID 67384983HCID 67384983, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A dried flask fitted with a condenser was charged with 2,7-dibromo-4-nitro-9,10-dihydro-phenanthrene (1.1) (45.00 g, 383.0 mmol), triphenylphosphine (77.04 g, 262.3 mmol) and 1,2-dichlorobenzene (235 cm3). The resulting mixture was refluxed for 4 hours until completion of reaction, then was cooled down and the solvent wasremoved in vacuo. The crude product was purified by column chromatography (gradient, 90:10 to 70:30; petroleum ether:ethyl acetate as eluent) and then recrystallized in a mixture of petroleum ether (80-100° C.) and toluene (ca. 1:1). (24.03 g, yield 57.2%): NMR (1H, 300 MHz, DMSO): δ 11.09 (s, 1H), 7.46 (d, J=0.9 Hz, 2H), 7.12 (d, J=0.9 Hz, 2H), 3.25 (s, 4H).

Workup

  1. customA dried flask fitted with a condenser
  2. temperatureThe resulting mixture was refluxed for 4 hours until completion of reaction
  3. temperaturewas cooled down
  4. customThe crude product was purified by column chromatography (gradient, 90:10 to 70:30; petroleum ether:ethyl acetate as eluent)
  5. customrecrystallized in a mixture of petroleum ether (80-100° C.) and toluene (ca. 1:1)

Sources & evidence

ORD record
ord-d9d3632a6b2f4b22a7259fd2d65a14c9
Source dataset
uspto-grants-2015_12
Patent number
US09212260B2

Reaction notes

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