Acetonitrile → 5-Bromo-2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran

HRID 1850371Notes

Reaction equation

HRID 1850371 reaction equation
[Br:1]N1C(=O)CCC1=O.C(#N)C.[CH3:12][C:13]1([CH3:25])[CH2:17][C:16]2[C:18]([CH3:24])=[CH:19][C:20]([CH3:23])=[C:21]([CH3:22])[C:15]=2[O:14]1>O>[Br:1][C:19]1[C:20]([CH3:23])=[C:21]([CH3:22])[C:15]2[O:14][C:13]([CH3:25])([CH3:12])[CH2:17][C:16]=2[C:18]=1[CH3:24]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 67184N-bromobutanimideHCID 117454372,2,4,6,7-Pentamethyl-2,3-dihydrobenzofuran

Product 1

HCID 667609285-Bromo-2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuranYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-bromosuccinimide (12.5 g, 70.0 mmol) was added to a solution of acetonitrile (165 mL) containing 2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran (11.1 g, 58.3 mmol) synthesized in Reference Example 3 under ice-cooling condition, and the mixture was warmed to room temperature. After stirring for 5 hours, water was added to the reaction solution. The generated precipitate was collected by filtration and washed with a mixture of acetonitrile/water (1/2). The solid was dried to give 13.5 g of the title compound (yield: 86%).

Workup

  1. customsynthesized in Reference Example 3 under ice-
  2. temperaturecooling condition
  3. filtrationThe generated precipitate was collected by filtration
  4. washwashed with a mixture of acetonitrile/water (1/2)
  5. customThe solid was dried

Sources & evidence

ORD record
ord-68e6d64275b441dc99a0b8d2cc5cc951
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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