4-Methoxybenzenesulfonyl chloride → 4-Methoxy-N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzenesulfonamide

HRID 1052452Notes

Reaction equation

HRID 1052452 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=2)[NH2:12])[O:3]1.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>>[CH3:17][O:18][C:19]1[CH:20]=[CH:21][C:22]([S:25]([NH:12][C:11]2[CH:13]=[CH:14][CH:15]=[C:9]([B:4]3[O:3][C:2]([CH3:16])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]3)[CH:10]=2)(=[O:27])=[O:26])=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 27346553-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 901029924-Methoxy-N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzenesulfonamideYield 99%

Procedure

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (450 mg, 2.05 mmol, prepared as described at Wing Kin Chow et al. Chemistry—A European Journal, 2011, 17(25), 6913-6917) was treated with 4-methoxybenzene-1-sulfonyl chloride (850 mg, 4.11 mmol) according to the method described In Preparation 15b to give 788 mg (99% yield) of the title compound as an oil. Purity 99%.

Sources & evidence

ORD record
ord-045e29d74b37453aaedc25ea15cc59e8
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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