Methanesulfonamide → N-(3-bromo-5-fluorobenzyl)methanesulfonamide

HRID 1187353Notes

Reaction equation

HRID 1187353 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH:5]=O.[CH3:11][S:12]([NH2:15])(=[O:14])=[O:13].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH2:5][NH:15][S:12]([CH3:11])(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 72879MethanesulfonamideHCID 5049666Sodium triacetoxyborohydrideHCID 219862463-Bromo-5-fluorobenzaldehyde

Product 1

HCID 47320493N-(3-bromo-5-fluorobenzyl)methanesulfonamideYield 93.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 3-bromo-5-fluorobenzaldehyde (LXXIX) (2.03 g, 10.01 mmol) in DCE (50 mL) was added methanesulfonamide (1.43 g, 15.01 mmol) and TEA (2.79 mL, 20.02 mmol). NaBH(OAc)3 (3.00 g, 14.13 mmol) was added and stirred at room temperature overnight. The solvent was removed under vacuum and the residue was partitioned between EtOAc and water. The organic layer separated and washed with water, brine, dried over MgSO4 and evaporated under vacuum to produce N-(3-bromo-5-fluorobenzyl)methanesulfonamide (LXXX) as a colorless oil (2.653 g, 9.40 mmol, 93.9% yield). ESIMS found C8H9BrFNO2S m/z 282.0 (M+H).

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue was partitioned between EtOAc and water
  3. customThe organic layer separated
  4. washwashed with water, brine
  5. dry with materialdried over MgSO4
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-3ce4fe8a685b46c08a771897e51ec482
Source dataset
uspto-grants-2014_03
Patent number
US08673936B2

Reaction notes

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