Methanesulfonyl chloride → N-(3-bromo-2-fluorophenyl)-N-(methylsulfonyl)methanesulfonamide

HRID 661879Notes

Reaction equation

HRID 661879 reaction equation
[Br:1][C:2]1[C:3]([F:9])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].CCN(C(C)C)C(C)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>C(Cl)Cl>[Br:1][C:2]1[C:3]([F:9])=[C:4]([N:5]([S:20]([CH3:19])(=[O:22])=[O:21])[S:20]([CH3:19])(=[O:22])=[O:21])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 223418913-Bromo-2-fluoroaniline2×

Product 1

HCID 59375038N-(3-bromo-2-fluorophenyl)-N-(methylsulfonyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-bromo-2-fluoroaniline (Intermediate 34-1, 160 mg, 0.842 mmol) and DIEA (0.368 mL, 2.105 mmol) in DCM (3 mL) was stirred at ca. −5° C. and treated with methanesulfonyl chloride (0.098 mL, 1.263 mmol) and stirred at that temperature for 2 h. The mixture was partitioned between DCM and NaHCO3 (aq). The organic phase was washed with brine, dried and concentrated to provide N-(3-bromo-2-fluorophenyl)-N-(methylsulfonyl)methanesulfonamide as a yellow solid (308 mg, quantitative), used without further purification. 1H NMR (400 MHz, chloroform-d) δ 7.70 (1H, ddd, J=8.1, 6.4, 1.5 Hz), 7.33 (1H, ddd, J=8.1, 6.5, 1.6 Hz), 7.15 (1H, td, J=8.1, 1.4 Hz), 3.46 (6H, s). Mass spectrum m/z 363, 365 (M+NH4)+.

Workup

  1. customThe mixture was partitioned between DCM and NaHCO3 (aq)
  2. washThe organic phase was washed with brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2a46b3614984486b951c7ef16cd5c82c
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

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