Sodium hydride → HCID 57443340, compound

HRID 2261824Notes

Reaction equation

HRID 2261824 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([OH:10])[CH:3]=1.[H-].[Na+]>C1COCC1.C(O)CCC>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][CH2:9][CH2:2][CH2:3][CH3:4])[CH:3]=1

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 129669614-Bromo-2-hydroxybenzonitrile

Product 1

HCID 57443340HCID 57443340, compoundYield 115%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-bromo-2-hydroxy-benzonitrile (0.89 g, 4.45 mmol) in THF (50 mL) and 1-butanol (2.0 mL) is slowly added to NaH (0.356 g, 8.90 mmol). The mixture is stirred at room temperature for one hour and quenched with water (10 mL). The mixture is concentrated, and the residue is extracted with ethyl acetate (20 mL×2). The combined organic layers are dried over sodium sulfate and concentrated to provide 4-bromo-2-butoxy-benzonitrile (0.65 g, 57%). 1H NMR (400 MHz, CDCl3): δ 7.37-7.34 (d, 1H), 7.11-7.08 (d, 1H), 7.08 (s, 1H), 4.04-4.01 (t, 2H), 1.80 (tt, 2H), 1.50 (tt, 2H), 0.95 (t, 3H).

Workup

  1. customquenched with water (10 mL)
  2. concentrationThe mixture is concentrated
  3. extractionthe residue is extracted with ethyl acetate (20 mL×2)
  4. dry with materialThe combined organic layers are dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e3186190f7e447c7ad65c0f1618cb715
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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