Water → HCID 23114133, compound

HRID 2376320Notes

Reaction equation

HRID 2376320 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2].[Br:11]N1C(=O)CCC1=O.O.BrC1C=CC(C(C)C)=CC=1O>C(=S)=S>[Br:11][C:5]1[C:4]([CH:1]([CH3:3])[CH3:2])=[CH:9][CH:8]=[CH:7][C:6]=1[OH:10]

Participants

6

Reactant 4

HCID 962WaterHCID 120593-IsopropylphenolHCID 67184N-bromobutanimideHCID 231138902-Bromo-5-(1-methylethyl)phenol

Product 1

HCID 23114133HCID 23114133, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a solution of 3-isopropylphenol (10.0 g, 73.4 mmol) in carbon disulfide (200 mL) was slowly added N-bromosuccinimide (13.1 g, 73.4 mmol) with ice-cooling, and the mixture was stirred for 1 hour. The reaction solution was stirred at room temperature for 1 hour, and then water was added thereto, which was extracted with ethyl acetate. The combined organic layer was washed with water and a saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=15:85) to obtain a mixture of 2-bromo-5-isopropylphenol and 2-bromo-3-isopropylphenol (3:1) 11.0 g (yield 70%).

Workup

  1. temperaturecooling
  2. stirringThe reaction solution was stirred at room temperature for 1 hour
  3. extractionwhich was extracted with ethyl acetate
  4. washThe combined organic layer was washed with water
  5. dry with materiala saturated brine, dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=15:85)
  8. customto obtain

Sources & evidence

ORD record
ord-3eed3d117ff54bc99e0a00ba790f4bf2
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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