Water → 2-Bromo-5-(4-t-butylphenyl)-4-hydroxy-3-methylcarbonylthiophene

HRID 2103816Notes

Reaction equation

HRID 2103816 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:12][CH:13]=[C:14]([C:17]([CH3:19])=[O:18])[C:15]=2[OH:16])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Br:20]N1C(=O)CCC1=O.O>C(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:20][C:13]1[S:12][C:11]([C:8]2[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:10][CH:9]=2)=[C:15]([OH:16])[C:14]=1[C:17]([CH3:19])=[O:18]

Participants

6

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 442072892-(4-t-Butylphenyl)-3-hydroxy-4-methylcarbonylthiophene

Product 1

HCID 670504602-Bromo-5-(4-t-butylphenyl)-4-hydroxy-3-methylcarbonylthiopheneYield 86%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 6212ChloroformSolvent

Procedure

2-(4-t-butylphenyl)-3-hydroxy-4-methylcarbonylthiophene (2.66 g, 9.7 mmol), N-bromosuccinimide (1.73 g, 9.7 mmol) and benzoyl peroxide (153 mg, 0.63 mmol) were heated with reflux for 2 hours in 65 ml of chloroform. Water was added, and the reaction solution was extracted three times with chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution, and then dried over anhydrous sodium sulfate. The obtained organic layer was concentrated, and then purified with a silica gel column chromatography (n-hexane/chloroform=3/2) to obtain the desired product as a yellow solid (2.93 g, yield 86%).

Workup

  1. extractionthe reaction solution was extracted three times with chloroform
  2. washthe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe obtained organic layer was concentrated
  5. custompurified with a silica gel column chromatography (n-hexane/chloroform=3/2)

Sources & evidence

ORD record
ord-dd552c7d2f754aa7ab09c0a762b06ad5
Source dataset
uspto-grants-2009_08
Patent number
US07576115B2

Reaction notes

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