Sodium hydride → HCID 54970854, compound

HRID 1364417Notes

Reaction equation

HRID 1364417 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].[H-].[Na+].[F:12][C:13]1[CH:20]=[CH:19][CH:18]=[C:17](F)[C:14]=1[C:15]#[N:16]>CN(C)C=O>[F:12][C:13]1[CH:20]=[CH:19][CH:18]=[C:17]([O:6][CH2:5][C:4]2[CH:7]=[CH:8][CH:9]=[C:2]([Br:1])[CH:3]=2)[C:14]=1[C:15]#[N:16]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 746952,6-DifluorobenzonitrileHCID 851413-Bromobenzyl alcohol

Product 1

HCID 54970854HCID 54970854, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

3-Bromobenzyl alcohol (1.45 mg; 7.9 mmol) in dimethylformamide was added to a cooled (0° C.) slurry of sodium hydride (316 mg; 7.9 mmol) in dimethylformamide under nitrogen atmosphere. The reaction mixture was slowly warmed to room temperature, stirred for 30 min. The reaction mixture was then added to a cooled (0° C.) solution of 2,6-difluorobenzonitrile in dimethylformamide, stirred for 2 hours at room temperature. The reaction mixture was poured on crushed ice-water, stirred, filtered, washed with water and dried to afford 1.81 grams of 2-fluoro-6-(3-bromophenylmethoxy)benzonitrile.

Workup

  1. additionThe reaction mixture was then added to
  2. stirringstirred for 2 hours at room temperature
  3. additionThe reaction mixture was poured
  4. stirringstirred
  5. filtrationfiltered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-bedd544e7b4a4782a2473962e67209f6
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

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