N-bromobutanimide → HCID 22935596, compound

HRID 1272284Notes

Reaction equation

HRID 1272284 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]1([CH3:28])[CH:14]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[C:13]2[C:22]([CH3:27])=[CH:23][C:24]([CH3:26])=[CH:25][C:12]=2[O:11]1>C(#N)C>[Br:1][C:23]1[C:24]([CH3:26])=[CH:25][C:12]2[O:11][C:10]([CH3:28])([CH3:9])[CH:14]([C:15]3[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=3)[C:13]=2[C:22]=1[CH3:27]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 22935597HCID 22935597, compound

Product 1

HCID 22935596HCID 22935596, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-bromosuccinimide (2.1 g, 11.6 mmol) was added to a solution of 2,2,4,6-tetramethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran (3.1 g, 11.6 mmol) in acetonitrile (30 ml) with ice cooling and the mixture was stirred at room temperature for 1.5 hours. The resulting mixture was concentrated under reduced pressure. After the remaining solids were removed with filtration, the filtrate was concentrated under reduced pressure. The residue was purified using silica gel column chromatography (hexane) to obtain 2.67 g (yield 67%) of the title compound via recrystallization (methanol). mp. 116–118° C.

Workup

  1. concentrationThe resulting mixture was concentrated under reduced pressure
  2. customAfter the remaining solids were removed with filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified

Sources & evidence

ORD record
ord-95ceecc40a0846f994224feb38f2e263
Source dataset
uspto-grants-2007_04
Patent number
US07208495B2

Reaction notes

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