Iodoethane → Methyl 6-bromo-3-ethoxy-2-methylbenzoate

HRID 577548Notes

Reaction equation

HRID 577548 reaction equation
[Br:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([CH3:12])[C:5]([OH:13])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:21][CH3:22].C(OCC)(=O)C>CN(C=O)C>[Br:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([CH3:12])[C:5]([O:13][CH2:21][CH3:22])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 77058981Methyl 6-bromo-3-hydroxy-2-methylbenzoate

Product 1

HCID 86723776Methyl 6-bromo-3-ethoxy-2-methylbenzoateYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of methyl 6-bromo-3-hydroxy-2-methylbenzoate (114b, 0.701 g, 2.86 mmol) in DMF (6 mL) was added cesium carbonate (0.997 g, 3.0 mmol) and then iodoethane (0.400 mL, 5.00 mmol). The reaction was stirred at 65° C. for 30 minutes. The reaction mixture was poured into ethyl acetate and washed with water (×2). The ethyl acetate layer was concentrated under vacuum to give methyl 6-bromo-3-ethoxy-2-methylbenzoate (114c, 0.75 g, 96% yield) as a clear oil.

Workup

  1. washwashed with water (×2)
  2. concentrationThe ethyl acetate layer was concentrated under vacuum

Sources & evidence

ORD record
ord-d6c42be0a4c14c7f8ea15a5f426d572a
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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