N-bromobutanimide → Ethyl 4-(bromomethyl)-3-(4-fluorophenyl)isoxazole-5-carboxylate

HRID 2388175Notes

Reaction equation

HRID 2388175 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH3:13])=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:10][N:9]=2)=[CH:4][CH:3]=1.C1C(=O)N([Br:26])C(=O)C1>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Br:26][CH2:13][C:12]1[C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[N:9][O:10][C:11]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 67530024Ethyl 3-(4-fluorophenyl)-4-methylisoxazole-5-carboxylate

Product 1

HCID 67529002Ethyl 4-(bromomethyl)-3-(4-fluorophenyl)isoxazole-5-carboxylateYield 109.5%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

Ethyl 3-(4-fluorophenyl)-4-methylisoxazole-5-carboxylate (8.6 g, 34.5 mmol), NBS (6.8 g, 38.0 mmol), and benzoyl peroxide (0.84 g, 3.45 mmol) were added to 200 mL of carbon tetrachloride and the mixture was refluxed for 16 h. The reaction mixture was filtered and the filtrate was removed in vacuo to give 12.4 g of the title compound. 1H NMR (CDCl3, 200 MHz): δ=9.21 (s, 1H), 7.75-7.85 (m, 2H), 7.22-7.32 (m, 2H), 4.66 (s, 2H), 4.54 (q, 2H, J=7.0 Hz), 1.41 (t, 3H, J=7.0 Hz).

Workup

  1. temperaturethe mixture was refluxed for 16 h
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was removed in vacuo

Sources & evidence

ORD record
ord-dedcbfe9549c404bba354c973a9d351f
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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