Boron tribromide → (3-(4-Hydroxyphenylsulfonamido)phenyl)boronic acid

HRID 1052508Notes

Reaction equation

HRID 1052508 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([B:19]3[O:23]C(C)(C)C(C)(C)[O:20]3)[CH:14]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C:13]2[CH:14]=[C:15]([B:19]([OH:23])[OH:20])[CH:16]=[CH:17][CH:18]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 901029924-Methoxy-N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzenesulfonamide

Product 1

HCID 90103182(3-(4-Hydroxyphenylsulfonamido)phenyl)boronic acidYield 23.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Methoxy-N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzenesulfonamide (168 mg, 0.43 mmol) was dissolved in dichloromethane (4 ml). A solution of boron tribromide (1M in dichloromethane, 4.32 mL, 4.32 mmol) was added dropwise and the reaction was stirred at room temperature overnight. The mixture was diluted with dichloromethane and washed with a solution of 4% sodium bicarbonate, water, brine and dried over sodium sulphate, filtered and evaporated under reduced pressure. The product was purified by reverse phase using SP1® Purification System to give 30 mg (23% yield) of the title compound. Purity 100%.

Workup

  1. washwashed with a solution of 4% sodium bicarbonate, water, brine
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe product was purified by reverse phase
  6. custom® Purification System

Sources & evidence

ORD record
ord-0b1089e3130c4f0199df94d557058a90
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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