Triphenylphosphine → [2-(3-Bromomethyl-phenoxymethyl)-6-methyl-phenoxy]-acetonitrile

HRID 892199Notes

Reaction equation

HRID 892199 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=1)[O:6][CH2:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:9]=1[O:10][CH2:11][C:12]#[N:13].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C(=O)N([Br:48])C(=O)C1>C1COCC1>[Br:48][CH2:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=1)[O:6][CH2:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:9]=1[O:10][CH2:11][C:12]#[N:13]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 22241439[2-(3-Hydroxymethyl-phenoxymethyl)-6-methyl-phenoxy]-acetonitrile

Product 1

HCID 22241568[2-(3-Bromomethyl-phenoxymethyl)-6-methyl-phenoxy]-acetonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [2-(3-hydroxymethyl-phenoxymethyl)-6-methyl-phenoxy]-acetonitrile (230 mg, 0.81 mmol, example 75) in THF (3 mL) is added Ph3P (233 mg, 0.89 mmol) and stirred until homogeneous. Cooled solution to 0° C. then added portionwise NBS (151 mg, 0.85 mmol) and let stir 45 min. Concentrated reaction mixture under reduced pressure. The residue is purified by flash chromatography (silica, 40% CH2Cl2 in hexanes) to give the title compound as a white crystalline solid. MS (EI) 345, 347 (M)+, Br pattern.

Workup

  1. stirringlet stir 45 min
  2. concentrationConcentrated
  3. customreaction mixture under reduced pressure
  4. customThe residue is purified by flash chromatography (silica, 40% CH2Cl2 in hexanes)

Sources & evidence

ORD record
ord-0d055507616f46738bedd137d1191f52
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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