Triphenylphosphine → 4-(3-Chloro-1-propyn-1-yl)-2-(methyloxy)-1-nitrobenzene

HRID 419479Notes

Reaction equation

HRID 419479 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]#[C:13][CH2:14]O)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C(=O)N([Cl:42])C(=O)C1>C(Cl)Cl>[Cl:42][CH2:14][C:13]#[C:12][C:5]1[CH:6]=[CH:7][C:8]([N+:9]([O-:11])=[O:10])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 31398ChlorosuccinimideHCID 594525753-[3-(Methyloxy)-4-nitrophenyl]-2-propyn-1-ol

Product 1

HCID 594529054-(3-Chloro-1-propyn-1-yl)-2-(methyloxy)-1-nitrobenzeneYield 97.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3-[3-(methyloxy)-4-nitrophenyl]-2-propyn-1-ol (1.6 g, 7.72 mmol) in 75 mL of DCM was added, triphenylphosphine (2.7 g, 10.27 mmol), and NCS (1.37 g, 10.27 mmol). The mixture stirred for 1 h. 10 g of silica gel was added. The solvent was rotovaped down and the pre-adsorbed solids were purified by flash chromatography to give the title compound of step B (1.7 g, 7.53 mmol, 97%). 1H NMR (400 MHz, CDCl3) δ ppm 7.80 (d, J=8.42 Hz, 1H), 7.13 (d, J=1.47 Hz, 1H), 7.08 (dd, J=8.33, 1.56 Hz, 1H), 4.37 (s, 2 H), 3.95 (s, 3H).

Workup

  1. addition10 g of silica gel was added
  2. customthe pre-adsorbed solids were purified by flash chromatography

Sources & evidence

ORD record
ord-e91231b71abd4dfb81bd463f4e1f6329
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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