Water → HCID 23114095, compound

HRID 2376271Notes

Reaction equation

HRID 2376271 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[C:14]3[C:15]([CH3:21])=[CH:16][C:17]([CH3:20])=[C:18]([CH3:19])[C:13]=3[O:12][CH2:11]2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].C([O-])(=O)C.[Na+].[Br:27]Br.O>C(#N)C>[Br:27][C:16]1[C:17]([CH3:20])=[C:18]([CH3:19])[C:13]2[O:12][CH2:11][CH:10]([C:7]3[CH:6]=[CH:5][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:9][CH:8]=3)[C:14]=2[C:15]=1[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 517045Sodium AcetateHCID 23113966HCID 23113966, compound

Product 1

HCID 23114095HCID 23114095, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 3-(4-isopropylphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran synthesized in Reference Example 13 (6.10 g, 21.8 mmol) and sodium acetate (1.97 g, 24.0 mmol) in acetonitrile (30 mL) was added bromine (1.17 mL, 22.9 mmol), and the mixture was stirred at the same temperature for 1 hour. Water was poured into the reaction mixture, which was extracted with ethyl acetate. The extract was washed with a saturated sodium hydrogen carbonate solution and water, dried over magnesium sulfate, filtered and then concentrated under reduced pressure. The obtained residue was crystallized from methanol to obtain 7.90 g (yield 99%) of the title compound. Melting point: 86-87° C. (methanol).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe extract was washed with a saturated sodium hydrogen carbonate solution and water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was crystallized from methanol

Sources & evidence

ORD record
ord-9408bc5018b945de83d8219769578500
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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