Water → HCID 23114308, compound

HRID 2376369Notes

Reaction equation

HRID 2376369 reaction equation
[CH:1]([C:4]1[CH:20]=[CH:19][C:7]([CH2:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[O:17][CH3:18])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[Br:21]N1C(=O)CCC1=O.O>C(#N)C>[Br:21][C:13]1[C:14]([CH3:15])=[C:9]([CH2:8][C:7]2[CH:19]=[CH:20][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=2)[C:10]([O:17][CH3:18])=[CH:11][C:12]=1[CH3:16]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 23114339HCID 23114339, compound

Product 1

HCID 23114308HCID 23114308, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(4-isopropylbenzyl)-1-methoxy-3,5-dimethylbenzene obtained in Reference Example 213 (3.45 g, 12.9 mmol) in acetonitrile (40 mL) was added N-bromosuccinimide (2.29 g, 12.9 mmol) with ice-cooling, and the mixture was stirred for 30 minutes. Water was added to the reaction solution, which was extracted with ethyl acetate, and then the organic layer was dried over anhydrous sodium sulfate, was filtered, and then was concentrated under reduced pressure. Ethyl acetate-hexane (1:9) was added to the residue, and the precipitated crystals were filtered, and the filtrate was concentrated to obtain 4.50 g (yield is quantitative) of the title compound. Oily matter.

Workup

  1. temperaturecooling
  2. extractionwas extracted with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. filtrationwas filtered
  5. concentrationwas concentrated under reduced pressure
  6. additionEthyl acetate-hexane (1:9) was added to the residue
  7. filtrationthe precipitated crystals were filtered
  8. concentrationthe filtrate was concentrated
  9. customto obtain

Sources & evidence

ORD record
ord-228b6f494a514e4385cb8b46395d92bf
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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