Iodoethane → HCID 86699746, compound

HRID 515178Notes

Reaction equation

HRID 515178 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:20](I)[CH3:21]>CN(C=O)C.O>[CH2:20]([O:7][C:6](=[O:8])[C:5]1[C:9]([CH3:11])=[CH:10][C:2]([Br:1])=[CH:3][C:4]=1[O:12][CH3:13])[CH3:21]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 454803864-Bromo-2-methoxy-6-methylbenzoic acid

Product 1

HCID 86699746HCID 86699746, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-bromo-2-methoxy-6-methyl-benzoic acid (synthesized according to the methods described in sections a) to d) of example 10) (10.7 g, 43.7 mmol) in DMF (90 ml) are added potassium carbonate (12.1 g, 87.3 mmol) and ethyl iodide (17.5 ml, 218 mmol) and the resulting mixture is stirred at room temperature for 2 h. After completion of reaction the reaction mixture is diluted with water (200 ml) and extracted with ethyl acetate (3×50 ml). The combined organic layers are washed with water (2×30 ml), brine (2×30 ml), dried over sodium sulfate and concentrated in vacuo yielding 4-bromo-2-methoxy-6-methyl-benzoic acid ethyl ester (10.5 g, 39 mmol, 89%).

Workup

  1. customAfter completion of reaction the reaction mixture
  2. extractionextracted with ethyl acetate (3×50 ml)
  3. washThe combined organic layers are washed with water (2×30 ml), brine (2×30 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3674c076dace4675a5d2b55f58989bb4
Source dataset
uspto-grants-2015_08
Patent number
US09108936B2

Reaction notes

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