Water → Ethyl 1-(4-bromo-3-methylisoxazol-5-YL)cyclopropane-1-carboxylate

HRID 1772371Notes

Reaction equation

HRID 1772371 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:9][CH2:8]2)[O:4][N:3]=1.[Br:15]N1C(=O)CCC1=O.O>CN(C=O)C>[Br:15][C:6]1[C:2]([CH3:1])=[N:3][O:4][C:5]=1[C:7]1([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 67811851HCID 67811851, compound

Product 1

HCID 67812454Ethyl 1-(4-bromo-3-methylisoxazol-5-YL)cyclopropane-1-carboxylateYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 1-(3-methylisoxazol-5-yl)cyclopropanecarboxylate (9.49 g, 48.6 mmol) in anhydrous DMF (50 mL) was added N-bromosuccinimide (10.31 g, 57.9 mmol). The reaction mixture was stirred at room temperature for 24 h. To the orange mixture was added water and the aqueous layer was extracted with MTBE (3×). The combined organic layers were washed with aqueous 10% sodium thiosulfate, water (2×) and dried to provide the product ethyl 1-(4-bromo-3-methylisoxazol-5-yl)cyclopropanecarboxylate (12.5 g, 45.6 mmol, 94% yield) as a light yellow oil. The product was used directly in the subsequent reaction without further purification. LC/MS m/z 274 [M+H]+.

Workup

  1. extractionthe aqueous layer was extracted with MTBE (3×)
  2. washThe combined organic layers were washed with aqueous 10% sodium thiosulfate, water (2×)
  3. customdried

Sources & evidence

ORD record
ord-ef3ad1ff22af4d288c40e55970208052
Source dataset
uspto-grants-2016_02
Patent number
US09249161B2

Reaction notes

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