Acetonitrile → HCID 9924988, compound

HRID 1797403Notes

Reaction equation

HRID 1797403 reaction equation
[Br:1]Br.[CH3:3][C:4]1([CH3:23])[CH:8]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[C:7]2[C:16]([CH3:22])=[CH:17][C:18]([CH3:21])=[C:19]([CH3:20])[C:6]=2[O:5]1.C([O-])(=O)C.[Na+].C(#N)C>O>[Br:1][C:17]1[C:18]([CH3:21])=[C:19]([CH3:20])[C:6]2[O:5][C:4]([CH3:23])([CH3:3])[CH:8]([C:9]3[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][CH:14]=3)[C:7]=2[C:16]=1[CH3:22]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 24408BromineHCID 517045Sodium AcetateHCID 10850374Benzofuran, 2,3-dihydro-2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-

Product 1

HCID 9924988HCID 9924988, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

Bromine (29.3 mL) was added dropwise to a mixture of 2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran (145 g), sodium acetate (50.9 g) and acetonitrile (2175 mL) at 0 to 5° C. The mixture was stirred at 0 to 10° C. for 1 hour and water (725 mL) was added thereto. Precipitated crystals were filtered to obtain the title the compound (175 g, 94.2%).

Workup

  1. customPrecipitated crystals
  2. filtrationwere filtered

Sources & evidence

ORD record
ord-1cccb8e68cac40d6bdcd0c589ec41195
Source dataset
uspto-grants-2006_04
Patent number
US07034166B2

Reaction notes

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