Triphenylphosphine → 2-Cyanomethoxy-3-methylbenzyl bromide

HRID 2117234Notes

Reaction equation

HRID 2117234 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:21][C:22]1[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[C:23]=1[O:24][CH2:25][C:26]#[N:27].[Br:33]N1C(=O)CCC1=O>C1COCC1>[Br:33][CH2:21][C:22]1[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[C:23]=1[O:24][CH2:25][C:26]#[N:27]

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-Hydroxymethyl-6-methyl-phenoxy)-acetonitrile (9.3 g, 52.5 mmoles) 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-30cda7b4f70248ce9f269319edceb241
Source dataset
uspto-grants-2008_10
Patent number
USRE040558E1

Reaction notes

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