Methanesulfonyl chloride → N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide

HRID 425937Notes

Reaction equation

HRID 425937 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[O:3]1.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>C(Cl)Cl.CN1CCOCC1.C(OCC)(=O)C>[CH3:8][C:6]1([CH3:7])[C:2]([CH3:16])([CH3:1])[O:3][B:4]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][S:18]([CH3:17])(=[O:20])=[O:19])=[CH:11][CH:10]=2)[O:5]1

Participants

6

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 16217653N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamideYield 93.3%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 79724-MethylmorpholineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (5.00 g, 22.8 mmol) in methylene chloride (100 mL) and 4-methylmorpholine (16 mL) at 0° C. was added methanesulfonyl chloride (2.1 mL, 28 mmol). The mixture was stirred at room temperature for 2 hr, and diluted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated to provide N-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanesulfonamide as a white solid (6.32 g, 93% yield). MS m/z 298 (M+1).

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-65ff7a4211d941d488742d0d3acef881
Source dataset
uspto-grants-2012_01
Patent number
US08106197B2

Reaction notes

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