Sodium hydride → 4-Bromo-2-(4-chloro-2-iodo-phenoxymethyl)-benzonitrile

HRID 2220225Notes

Reaction equation

HRID 2220225 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH2:10]Br)[CH:3]=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([I:20])[CH:14]=1.[H-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH2:10][O:19][C:16]2[CH:17]=[CH:18][C:13]([Cl:12])=[CH:14][C:15]=2[I:20])[CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 6202344-Chloro-2-iodophenol2×HCID 251406084-Bromo-2-(bromomethyl)benzonitrile2×

Product 1

HCID 688932114-Bromo-2-(4-chloro-2-iodo-phenoxymethyl)-benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 4-Bromo-2-bromomethyl-benzonitrile Example 347A (1.00 g, 3.64 mmol) and 4-Chloro-2-iodo-phenol Example 347B (0.94 g, 3.69 mmol) in dry DMF (8.0 mL) under argon was added 95% NaH (103 mg, 4.08 mmol). The reaction mixture was stirred at room temperature for 2.5 hours and quenched with water (30 mL). The resulting mixture was extracted with ether (180 mL). The organic layer was washed with water (1×30 mL), 1N NaOH solution (1×30 mL) and brine (1×30 mL). The organic layer was dried (MgSO4), filtered and concentrated in vacuo to give 614 mg of crude 4-Bromo-2-(4-chloro-2-iodo-phenoxymethyl)-benzonitrile Example 347C which was used as is for the next transformation.

Workup

  1. customquenched with water (30 mL)
  2. extractionThe resulting mixture was extracted with ether (180 mL)
  3. washThe organic layer was washed with water (1×30 mL), 1N NaOH solution (1×30 mL) and brine (1×30 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f6151239b55942a4a65ff780321d16da
Source dataset
uspto-grants-2008_08
Patent number
US07417040B2

Reaction notes

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