Phenylboronic Acid → 4-Phenylbenzene-1-sulfonamide

HRID 2421651Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[C:12]1([C:2]2[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][CH:3]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Reactant 2

HCID 66827Phenylboronic Acid

HCID 696964-Bromobenzenesulfonamide

Product 1

HCID 50171404-Phenylbenzene-1-sulfonamideYield 56.6%

Procedure

Using preparation method 2, 4-bromobenzenesulfonamide (472 mg, 2 mmol) was reacted with phenylboronic acid (268 mg, 2.2 mmol). Purification by washing with hot toluene followed by filtration gave 4-phenylbenzenesulfonamide as an off-white crystalline solid (264 mg, 55%). NMR 1H (ppm, CDCl3): 7.87 (d, J3=8.6 Hz, 2H), 7.83 (d, J3=8.7 Hz, 2H), 7.70 (d, J3=7.2 Hz, 2H), 7.48 (t, J3=7.3 Hz), 7.40 (t, J3=7.1 Hz, 1H).

Workup

customPurification
washby washing with hot toluene
filtrationfollowed by filtration

Sources & evidence

ORD record: ord-a6c571c4e72943d0b03ce41e1644fa23
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07956216B2

Reaction notes

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