Hydrochloric Acid → 4-((Methylamino)sulphonyl)benzene boronic acid

HRID 17969

Reaction equation

HRID 17969 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[B:13](OC(C)C)([O:18]C(C)C)[O:14]C(C)C.[Li]CCCC.Cl>C1COCC1>[CH3:12][NH:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([B:13]([OH:18])[OH:14])=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 1012154-bromo-N-methylbenzene-1-sulfonamideHCID 178418339Butyllithium

Product 1

HCID 441187634-((Methylamino)sulphonyl)benzene boronic acidYield 104.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-bromo-N-methyl-benzene sulfonamide (24.9 g, 0.1 mol) and B(OiPr)3 (28.2 g, 0.15 mol) in THF (200 mL) was added n-BuLi (100 mL, 0.25 mol) at −70° C. The mixture was slowly warmed to 0° C., then 10% HCl solution was added until pH 3˜4. The resulting mixture was extracted with EtOAc. The organic layer was dried over Na2SO4, and evaporated under reduced pressure to give 4-(N-methylsulfamoyl)phenylboronic acid (22.5 g, 96%), which was used in the next step without further purification. 1H NMR (DMSO-d6, 300 MHz) δ 8.29 (s, 2H), 7.92 (d, J=8.1 Hz, 2H), 7.69 (d, J=8.4 Hz, 2H), 2.36 (d, J=5.1 Hz, 3H).

Workup

  1. extractionThe resulting mixture was extracted with EtOAc
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-6308b021400e4046b19ed29fea48dfda
Source dataset
uspto-grants-2010_06
Patent number
US07741321B2

Linked notes

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