N-bromobutanimide → 2-Bromo-1-fluoro-4-(methylsulfonyl)benzene

HRID 633532Notes

Reaction equation

HRID 633532 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Br:12]N1C(=O)CCC1=O>S(=O)(=O)(O)O>[Br:12][C:7]1[CH:6]=[C:5]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:4]=[CH:3][C:2]=1[F:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 679941-Fluoro-4-(methylsulphonyl)benzene

Product 1

HCID 673870812-Bromo-1-fluoro-4-(methylsulfonyl)benzeneYield 96%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

1-Fluoro-4-(methylsulfonyl)benzene (5.0 g, 28.7 mmol) in conc. sulfuric acid (30 mL) was cooled to 0° C. To this solution was added N-bromosuccinimide (5.62 g, 31.6 mmol). The reaction mixture was stirred at room temperature for 6 hours and then poured into ice-water. The resulting solid was collected by filtration, washed with cold water three times, and dried in a vacuum oven overnight to give the title compound (6.95 g, 27.5 mmol, 96% yield).

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. washwashed with cold water three times
  3. customdried in a vacuum oven overnight

Sources & evidence

ORD record
ord-fd4d5289b6704b35a771c98bd16b7927
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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