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

HRID 589453Notes

Reaction equation

HRID 589453 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 99%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Preparation of 3-bromo-5-fluorobenzaldehyde (XLIX) (2.03 g, 10.0 mmol) in DCE (50 mL) was added methanesulfonamide (1.43 g, 15.0 mmol) and TEA (2.79 mL, 20.0 mmol). The solution was stirred for a few minutes before NaBH(OAc)3 (3.00 g, 14.1 mmol) was added. The reaction was stirred at room temperature overnight. The solvent was removed under vacuum and the residue was partitioned between EtOAc and water. The organic layer was separated, dried over MgSO4 and evaporated under vacuum to give N-(3-bromo-5-fluorobenzyl)methanesulfonamide (L) as a clear oil (2.65 g, 9.39 mmol, 99% yield). ESIMS found C8H9BrFNO2S m/z 282 (M+H).

Workup

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

Sources & evidence

ORD record
ord-f52496bc37724f498712e45f2e2f0a2b
Source dataset
uspto-grants-2016_01
Patent number
US09233104B2

Reaction notes

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