N-bromobutanimide → HCID 59363842, compound

HRID 1430645Notes

Reaction equation

HRID 1430645 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[CH3:5].[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:16])[C:4]([Br:17])([C:6]1[CH:11]=[CH:10][C:9]([S:12]([CH3:15])(=[O:13])=[O:14])=[CH:8][CH:7]=1)[CH3:5]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 59363826HCID 59363826, compound

Product 1

HCID 59363842HCID 59363842, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

Mixture of 2-(4-Methanesulfonyl-phenyl)-propionic acid methyl ester (0.939 g, 0.3.88 mmol), N-bromosuccinimide (0.69 g, 3.88 mmol) and catalytic amount of benzoyl peroxide (0.01 g) in carbon tetrachloride (75 ml) was refluxed for 1 hour under nitrogen atmosphere, RM was cooled to room temperature and poured onto water (50 ml) under stirring, layer separated, organic layer was washed with water (2×25 ml). Removal of solvent gave the 2-Bromo-2-(4-methanesulfonyl-phenyl)-propionic acid methyl ester (1.22 g) as white solid which was used for the next step without further purification. 1H NMR (400 MHz, CDCl3): δ 2.32 (s, 3H), 3.08 (s, 3H), 3.82 (s, 3H), 7.78 (d, J=8.4 Hz, 2H), 7.94 (d, J=8.4 Hz, 2H).

Workup

  1. temperaturewas refluxed for 1 hour under nitrogen atmosphere
  2. additionpoured onto water (50 ml)
  3. customlayer separated
  4. washorganic layer was washed with water (2×25 ml)
  5. customRemoval of solvent

Sources & evidence

ORD record
ord-46e8505d5c44463e8924d259b3813838
Source dataset
uspto-grants-2015_01
Patent number
US08940900B2

Reaction notes

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