Sodium hydride → 3-(o-Bromobenzyloxy)4-methoxybenzonitrile

HRID 353049

Reaction equation

HRID 353049 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[H-].[Na+].F[C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[C:16]#[N:17]>CN(C=O)C>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][O:5][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[C:16]#[N:17]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 728502-Bromobenzyl alcoholHCID 27745483-Fluoro-4-methoxybenzonitrile

Product 1

HCID 227070173-(o-Bromobenzyloxy)4-methoxybenzonitrileYield 71.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-bromobenzyl alcohol (16.50 g, 88.2 mmol) in DMF (100 ml) was added sodium hydride (60% dispersion in mineral oil, 2.94 g, 73.5 mmol) and this was followed by 3-fluoro-4-methoxybenzonitrile (8.88 g, 58.8 mmol) and the resulting mixture was heated to 90° C. for 2 h under N2. After cooling, the mixture was partitioned between ether and H2O, the organic layer washed sequentially with 0.5 N HCl and saturated brine and then dried over MgSO4. Trituration with ether/pentane (1/3, v/v) afforded the subtitle compound as an off-white solid (13.35 g, 71%). Rf 0.27 (hexane/EtOAc 5/1, v/v). MS m/z 318, 320 (MH+).

Workup

  1. temperatureAfter cooling
  2. customthe mixture was partitioned between ether and H2O
  3. washthe organic layer washed sequentially with 0.5 N HCl and saturated brine
  4. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-cf4eb2fcce58450c9e5b5f962b9df908
Source dataset
uspto-grants-2004_06
Patent number
US06750214B2

Linked notes

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