N-bromobutanimide → HCID 57155465, compound

HRID 1170042Notes

Reaction equation

HRID 1170042 reaction equation
[C:1]([O:5][C:6](=[O:19])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:9]=1[O:15][C:16]([CH3:18])=[O:17])([CH3:4])([CH3:3])[CH3:2].[Br:20]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[C:1]([O:5][C:6](=[O:19])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][Br:20])=[CH:10][C:9]=1[O:15][C:16]([CH3:18])=[O:17])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 57109643HCID 57109643, compound

Product 1

HCID 57155465HCID 57155465, compoundYield 38.9%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 2-(2-acetoxyl-4-methylphenyl)acetic acid tert-butyl ester (4.9 g, 18.5 mmol) in CCl4 (50 ml) was added N-bromosuccinimide (3.29 g, 18.5 mmol, 1 equivalents) and benzoyl peroxide (100 mg), the reaction mixture was refluxed under argon for 3 hr. The reaction mixture was then cooled to room temperature. The solid precipitate was filtered off, and washed with hexanes, the combined organic was taken to dryness, and the residue obtained was purified by chromatography (Hexanes—EtOAc, 50:1 to 40:1) to give (2-acetoxyl-4-bromomethylphenyl)acetic acid tert-butyl ester 2.467 g (38.8% yield) as an oil. 1H NMR (CDCl3) δ: 7.290 (1H, d, J=7.81 Hz), 7.230 (1H, dd, J=1.71, 7.81 Hz), 7.158 (1H, d, J=1.71 Hz), 4.467 (2H, s), 3.462 (2H, S), 2.320 (3H, s), 1.430 (9H, s) ppm. FABMS (+Ve), m/z 345 [MH+, 81Br], 343 [MH+, 79Br], 389 [MH+—C4H8, 81Br], 387 [MH+—C4H8, 79Br]. Anal. calcd. for C15H19BrO4: C, 52.5; H, 5.6; Br, 23.3. Found: C, 52.30; H, 5.50; Br, 23.44.

Workup

  1. temperaturethe reaction mixture was refluxed under argon for 3 hr
  2. filtrationThe solid precipitate was filtered off
  3. washwashed with hexanes
  4. customthe residue obtained
  5. customwas purified by chromatography (Hexanes—EtOAc, 50:1 to 40:1)

Sources & evidence

ORD record
ord-4f528be1ba7442eda0d0bac464b8eaa5
Source dataset
uspto-grants-2010_11
Patent number
US07825216B2

Reaction notes

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