Triphenylphosphine → 191602-52-5

HRID 1107282Notes

Reaction equation

HRID 1107282 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([CH2:11][CH2:12]O)[C:3]=1[OH:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[Br:1][C:2]1[C:3]2[O:14][CH2:12][CH2:11][C:4]=2[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 18787032HCID 18787032, compound

Product 1

HCID 18787034191602-52-5Yield 68.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-Bromo-6-(2-hydroxyethyl)-4-nitrophenol (3.12 g) was dissolved in tetrahydrofuran (20 ml) and was added dropwise to a cooled (0° C.) solution of triphenylphosphine (4.03 g) and diethylazodicarboxylate (2.43 ml) in tetrahydrofuran (30 ml). The mixture was stirred for 3 h and the solvent was removed in vacuo. The residue was purified on silica using 15% ethyl acetate in hexane as eluent to afford the title compound as a white crystalline solid (2 g). 1H NMR (250 MHz, CDCl3) δ 3.43 (2H, t, J=8.7 Hz), 4.85 (2H, t, J=9 Hz), 8.03-8.05 (1H, m), 8.20-8.29 (1H, m).

Workup

  1. additionwas added dropwise to
  2. customthe solvent was removed in vacuo
  3. customThe residue was purified on silica using 15% ethyl acetate in hexane as eluent

Sources & evidence

ORD record
ord-f3cf62b45612497a8923c8c9dc6c4cfa
Source dataset
uspto-grants-2000_05
Patent number
US06060469

Reaction notes

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