Bromine → 1-(4-Bromo-5-methyl-thiophen-2-yl)-ethanone

HRID 68564

Reaction equation

HRID 68564 reaction equation
[Br:1]Br.[C:3]([C:6]1[S:7][C:8]([CH3:11])=[CH:9][CH:10]=1)(=[O:5])[CH3:4].CC([O-])=O.[Na+]>O>[Br:1][C:9]1[CH:10]=[C:6]([C:3](=[O:5])[CH3:4])[S:7][C:8]=1[CH3:11]

Participants

5

Reactant 3

HCID 24408BromineHCID 836552-Acetyl-5-methylthiopheneHCID 517045Sodium Acetate

Product 1

HCID 126824981-(4-Bromo-5-methyl-thiophen-2-yl)-ethanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Bromine (9.7 ml) is added to a solution of 2-acetyl-5-methylthiophene (26.6 g) and NaOAc (17.2 g) in water (100 ml) at room temperature. After 12 hours at room temperature the reaction is quenched with a 1M aqueous solution of sodium thiosulfate (100 ml) and extracted three times with ethyl acetate (250 ml). The organic phases are combined, washed with a saturated aqueous solution of NaCl, dried over MgSO4 and concentrated in vacuo to yield 1-(4-bromo-5-methyl-thiophen-2-yl)-ethanone (41.8 g) as a brown oil. The crude product is used without further purification.

Workup

  1. customAfter 12 hours at room temperature the reaction is quenched with a 1M aqueous solution of sodium thiosulfate (100 ml)
  2. extractionextracted three times with ethyl acetate (250 ml)
  3. washwashed with a saturated aqueous solution of NaCl
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-68c430e4a3714df4bd2072ebb2c5aab6
Source dataset
uspto-grants-2014_09
Patent number
US08822466B2

Linked notes

Loading…