N-bromobutanimide → HCID 11463276, compound

HRID 1765441Notes

Reaction equation

HRID 1765441 reaction equation
[C:1]([O:5][C:6](=[O:22])[CH:7]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])([CH3:4])([CH3:3])[CH3:2].[Br:23]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[C:11]([O:10][C:8](=[O:9])[CH:7]([C:15]1[CH:20]=[CH:19][C:18]([CH2:21][Br:23])=[CH:17][CH:16]=1)[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:22])([CH3:13])([CH3:14])[CH3:12]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 11208981HCID 11208981, compound

Product 1

HCID 11463276HCID 11463276, compoundYield 66.5%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

p-Tolyl-malonic acid di-tert-butyl ester (5.695 g, 16.6 mmol) was dissolved in 80 ml of CCl4. To the solution was added N-bromosuccinimide (3.309 g, 16.6 mmol, 1 equivalents) and benzoyl peroxide (220 mg), the reaction mixture was refluxed under argon overnight; the reaction mixture was then cooled to room temperature, and the precipitate that had formed was filtered and washed with hexanes. The combined organic portions was dried, and the residue obtained was purified by chromatography to give (4-bromomethylphenyl)-malonic acid di-tert-butyl ester 4.2559 g (59.5% yield) as white solid. 1H NMR (CDCl3) δ: 7.379 (4H, s), 4.493 (2H, s), 4.435 (1H, s), 1.473 (18H, s) ppm. FABMS (+Ve), m/z 387 [MH+, 81Br], 385 [MH+, 79Br], 331 [MH+—C4H8, 81Br], 329 [MH+—C4H8. 79Br], 275 [MH+—2C4H8, 81Br], 273 [MH+—2C4H8, 79Br]. Anal. calcd. for C18H25BrO4: C, 56.1; H,6.5; Br, 20.7. Found: C, 55.52; H, 6.38; Br, 21.85.

Workup

  1. temperaturethe reaction mixture was refluxed under argon overnight
  2. customthe precipitate that had formed
  3. filtrationwas filtered
  4. washwashed with hexanes
  5. customThe combined organic portions was dried
  6. customthe residue obtained
  7. customwas purified by chromatography

Sources & evidence

ORD record
ord-944ac6b57fa74912a365e60f6564836f
Source dataset
uspto-grants-2007_06
Patent number
US07226991B1

Reaction notes

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