Sodium hydride → 4-Bromo-2-hydroxybenzonitrile

HRID 1519636Notes

Reaction equation

HRID 1519636 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4](F)[CH:3]=1.CS(CCO)(=O)=[O:13].[H-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([OH:13])[CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 848342-(Methylsulfonyl)ethanolHCID 7360294-Bromo-2-fluorobenzonitrile

Product 1

HCID 129669614-Bromo-2-hydroxybenzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-bromo-2-fluorobenzonitrile (4.0 g, 20 mmol) in DMF (20 mL) was added 2-(methylsulfonyl)ethanol (3.7 g, 30 mmol) and then NaH (2.4 g, 60% in mineral, 60 mmol) in portions at 0° C. The mixture was then warmed to rt. and quenched with 1N HCl, and extracted by EtOAc. The organic layers were washed with brine and dried over sodium sulfate, concentrated to give 4-bromo-2-hydroxybenzonitrile. 1H-NMR (400 MHz, DMSO) δ 7.55-7.57 (d, J=8.61 Hz, 1H), 7.16 (s, 1H), 7.11-7.13 (m, 1H).

Workup

  1. customat 0° C
  2. customand quenched with 1N HCl
  3. extractionextracted by EtOAc
  4. washThe organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-563852b9764b42c0a294e2e375a86197
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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