Benzyl Bromide → 3-Benzyloxy-4-cyano-benzoic acid methyl ester

HRID 1421742Notes

Reaction equation

HRID 1421742 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[C:6]([OH:12])[CH:5]=1.[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[C:6]([O:12][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:5]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 16641129Methyl 4-cyano-3-hydroxybenzoate

Product 1

HCID 538707413-Benzyloxy-4-cyano-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-cyano-3-hydroxybenzoic acid methyl ester, Example 34, Step 3 (300 mg, 1.7 mmol) was dissolved in DMF (8.5 ml) and treated with benzyl bromide (200 μl, 1.7 mmol). Cs2CO3 (610 mg, 1.87 mmol) was then added and the reaction mixture stirred at room temp. for 6 hours. The mixture was filtered and washed with DMF (3×10 mL). The solvent was removed in vacuo and the residue was purified by flash chromatography (15% EtOAc/Hexane) to yield the desired product.

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with DMF (3×10 mL)
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by flash chromatography (15% EtOAc/Hexane)

Sources & evidence

ORD record
ord-5d1c7e1585284ac7902edc6329df86ce
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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