N-bromobutanimide → HCID 57155465, compound

HRID 1765447Notes

Reaction equation

HRID 1765447 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](=[O:17])[CH3:18])([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-acetoxy-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, 550; 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-7f9b848691684de6a7598f2343e09b48
Source dataset
uspto-grants-2007_06
Patent number
US07226991B1

Reaction notes

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