N-bromobutanimide → HCID 11463276, compound

HRID 1170036Notes

Reaction equation

HRID 1170036 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 (59.50% 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-c6986d06670a417d92c25c2134611bd2
Source dataset
uspto-grants-2010_11
Patent number
US07825216B2

Reaction notes

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