N-bromobutanimide → HCID 18456634, compound

HRID 1272063Notes

Reaction equation

HRID 1272063 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH2:10][C:11]([NH:13][CH3:14])=[O:12].C1C(=O)N([Br:22])C(=O)C1.C(OOCC1C=CC=CC=1)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:22][CH:10]([C:3]1[CH:4]=[CH:5][C:6]([O:8][CH3:9])=[CH:7][C:2]=1[Cl:1])[C:11]([NH:13][CH3:14])=[O:12]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 11229634Benzyl PeroxideHCID 18456580HCID 18456580, compound

Product 1

HCID 18456634HCID 18456634, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-(2-chloro-4-methoxy-phenyl)-N-methyl-acetamide (70a) (0.22 g, 1.03 mmol), NBS (183 mg, 1.03 mmol), and 70% benzyl peroxide (36 mg, 0.103 mmol) in 6 mL of CCl4 was refluxed at 80° C. for three hours, cooled to room temperature, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography eluting with 1:1 EtOAc and hexanes to provide 185 mg white solid as the intermediate 70b. 1H NMR (300 MHz, CDCl3) δ 7.42 (d, 1H, J=8.85 Hz), 6.90 (d, 1H, J=2.63 Hz), 6.83–6.76 (m, 1H), 5.83 (s, 1H), 3.78 (s, 3H), 2.90 (d, 3H, J=4.90 Hz). LCMS (ESI+) [M+H]/z Calc'd 294, found 294.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash column chromatography
  5. washeluting with 1:1 EtOAc and hexanes

Sources & evidence

ORD record
ord-ef7ead49c3a64ae59857a9f997bc1010
Source dataset
uspto-grants-2007_04
Patent number
US07208500B2

Reaction notes

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