N-bromobutanimide → HCID 22556958, compound

HRID 983798Notes

Reaction equation

HRID 983798 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:4][C:3]=1[C:13](=[O:22])[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Br:23]N1C(=O)CCC1=O>CN(C=O)C.CCOCC>[Br:23][C:7]1[CH:6]=[C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])[CH:4]=[C:3]([C:13](=[O:22])[CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:2]=1[OH:1]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 22556924HCID 22556924, compound

Product 1

HCID 22556958HCID 22556958, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

The carboxylic acid 209, for example 3-[4-Hydroxy-3-(3-phenyl-propionyl)-phenyl]-propionic acid, (1.04 gm, 3.4 g mmol) was dissolved in DMF (7 mL) and N-bromosuccinimide (0.65 g, 3.66 mmol) was added to the solution. The mixture was stirred at ambient temperature for 2.5 h, diluted with ether and the organic layer was separated and washed with water and brine and then filtered through a pad of magnesium sulfate and concentrated. The residue was purified by flash chromatography (3.5:1.5:0.1 of hexane:ethyl acetate:acetic acid) to give 0.5 g of 3-[3-bromo-4-hydroxy-5-(3-phenyl-propionyl)-phenyl]-propionic acid 210 as a yellow-brown oil.

Workup

  1. customthe organic layer was separated
  2. washwashed with water and brine
  3. filtrationfiltered through a pad of magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (3.5:1.5:0.1 of hexane:ethyl acetate:acetic acid)

Sources & evidence

ORD record
ord-1a96b51472de479484bf5e0c72cd6dfe
Source dataset
uspto-grants-2005_03
Patent number
US06867200B1

Reaction notes

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