Allyl bromide → Methyl 2-(allyloxy)-4-methoxybenzoate

HRID 1864734

Reaction equation

HRID 1864734 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:13])[C:6](=[CH:11][CH:12]=1)[C:7]([O:9][CH3:10])=[O:8].C([O-])([O-])=O.[Cs+].[Cs+].[CH2:20](Br)[CH:21]=[CH2:22]>CN(C=O)C.CCOC(C)=O>[CH2:22]([O:13][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])[CH:21]=[CH2:20]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 79523Methyl 4-methoxysalicylate

Product 1

HCID 10242646Methyl 2-(allyloxy)-4-methoxybenzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 4-methoxysalicylate (2.0 g, 11 mmol) in DMF (20 mL) at room temperature was added Cs2CO3 (1.3 eq, 4.7 g) and allyl bromide (1.3 eq, 1.23 mL). After 2 hr, reaction mixture was diluted with EtOAc and washed with water (3×), brine (1×). The organic layer was dried over Na2SO4 and concentrated to provide the product as a pale yellow oil. Product was used without further purification.

Workup

  1. customreaction mixture
  2. washwashed with water (3×), brine (1×)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d59ac7b80e7844719da3b652a4e54201
Source dataset
uspto-grants-2009_12
Patent number
US07625933B2

Linked notes

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