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

HRID 478612

Reaction equation

HRID 478612 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 0.5N 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 0.5N HCl and saturated brine
  4. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-37301b24540e494493599c8b813ae6cb
Source dataset
uspto-grants-2003_11
Patent number
US06642242B2

Linked notes

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