4-(Bromomethyl)benzonitrile → HCID 14774146, compound

HRID 842806Notes

Reaction equation

HRID 842806 reaction equation
O.O.O.O.O.[N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][C:7]=1[CH2:16][O:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][CH:24]=1)[O-:21].[Na+].[C:26]([C:28]1[CH:35]=[CH:34][C:31]([CH2:32]Br)=[CH:30][CH:29]=1)#[N:27].O.CCOCC>CN(C=O)C>[N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][C:7]=1[CH2:16][O:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][CH:24]=1)[O:21][CH2:32][C:31]1[CH:34]=[CH:35][C:28]([C:26]#[N:27])=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 869964-(Bromomethyl)benzonitrileHCID 21584184Diethylether waterHCID 23684420HCID 23684420, compound

Product 1

HCID 14774146HCID 14774146, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 7.24 g (19.92 mmol) of sodium 3-(2quinolinylmethyloxy)phenoxide pentahydrate and 4.68 g (23.90 mmol) of p-cyanobenzyl bromide in 34 ml of dry DMF is stirred at 75° C. under nitrogen for 2 days. The reaction mixture is cooled to room temperature, then poured into 400 ml of 3:1 H2O/Et2O, shaken; and the phases separated. The aqueous layer is extracted and washed with 1:1 brine/H2O and brine. The ether solution is dried over 1:1 Na2SO4MgSO4, filtered and concentrated. The crude product is recrystallized from 70% EtOAc/hexane to obtain 4-(3-(2quinolinylmethyloxy)phenoxy-methyl)benzonitrile. (M.P. 112.5° C.)

Workup

  1. customand the phases separated
  2. extractionThe aqueous layer is extracted
  3. washwashed with 1:1 brine/H2O and brine
  4. dry with materialThe ether solution is dried over 1:1 Na2SO4MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product is recrystallized from 70% EtOAc/hexane

Sources & evidence

ORD record
ord-a19f8d62b6be4581b2108e45c2c04c07
Source dataset
uspto-grants-2002_04
Patent number
US06376512B1

Reaction notes

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