Triphenylphosphine → 2-Cyanomethoxy-3-methylbenzyl bromide

HRID 892152Notes

Reaction equation

HRID 892152 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([CH2:22][O:23][C:24]1[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][C:25]=1[CH2:26]O)#[N:21].[Br:33]N1C(=O)CCC1=O>C1COCC1>[Br:33][CH2:26][C:25]1[CH:28]=[CH:29][CH:30]=[C:31]([CH3:32])[C:24]=1[O:23][CH2:22][C:20]#[N:21]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 222413612-Cyanomethoxy-3-methylbenzylalcohol

Product 1

HCID 222414892-Cyanomethoxy-3-methylbenzyl bromide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Triphenylphosphine (15.2 g, 57.8 mmoles) is added to 2-cyanomethoxy-3-methylbenzylalcohol (9.3 g, 52.5 mmoles, example 23) in THF (175 mL). The mixture is stirred until homogeneous and cooled to 0° C., followed by addition, in three portions, of N-bromosuccinimide (10.3 g, 57.8 mmoles). After 90 minutes the reaction is concentrated and the residue purified by column chromatography (silica, 5:1 hex: EtOAc) to yield the title compound as a pale yellow crystalline solid. MS (EI) 239, 241 (M)+, Br pattern.

Workup

  1. concentrationAfter 90 minutes the reaction is concentrated
  2. customthe residue purified by column chromatography (silica, 5:1 hex: EtOAc)

Sources & evidence

ORD record
ord-42245a7af9094defa2d93a54820a9fce
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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