4-Methylbenzenethiol → Benzaldehyde, 5-bromo-2-[(4-methylphenyl)thio]-

HRID 1058654Notes

Reaction equation

HRID 1058654 reaction equation
[C:1]1([CH3:8])[CH:6]=[CH:5][C:4]([SH:7])=[CH:3][CH:2]=1.[Br:9][C:10]1[CH:11]=[CH:12][C:13](F)=[C:14]([CH:17]=1)[CH:15]=[O:16]>[OH-].[Na+].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[Br:9][C:10]1[CH:11]=[CH:12][C:13]([S:7][C:4]2[CH:5]=[CH:6][C:1]([CH3:8])=[CH:2][CH:3]=2)=[C:14]([CH:17]=1)[CH:15]=[O:16]

Participants

6

Reactant 2

HCID 78114-MethylbenzenethiolHCID 7363275-Bromo-2-fluorobenzaldehyde

Product 1

HCID 18668950Benzaldehyde, 5-bromo-2-[(4-methylphenyl)thio]-Yield 74.9%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolventHCID 14798Sodium HydroxideSolvent

Procedure

p-Toluenethiol (0.12 g, 1.0 mmol) was dissolved in a 10% sodium hydroxide aqueous solution (1.7 mL), and tetrabutylammonium bromide (0.016 g, 0.05 mmol) was added thereto, followed by stirring at room temperature for 5 minutes. 5-Bromo-2-fluorobenzaldehyde (0.2 g, 1.0 mmol) dissolved in toluene (1.7 mL) was added thereto by dropping, followed by stirring at room temperature for 4 hours. After the conventional treatment, and was recrystallized and purified with ethanol and hexane, to give 5-bromo-2-[(4-methylphenyl)thio]benzaldehyde (0.23 g, 74.1%).

Workup

  1. additionwas added
  2. additionwas added
  3. stirringby stirring at room temperature for 4 hours
  4. customAfter the conventional treatment, and was recrystallized
  5. custompurified with ethanol and hexane

Sources & evidence

ORD record
ord-b8581a503ce545cd9c05bea82cc8177e
Source dataset
uspto-grants-2003_02
Patent number
US06518268B1

Reaction notes

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