Boron tribromide → HCID 90102924, compound

HRID 1052544Notes

Reaction equation

HRID 1052544 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:6]=[C:7]([O:9]C)[CH:8]=1.B(Br)(Br)Br>ClCCl.C(OCC)(=O)C>[OH:2][C:3]1[CH:4]=[C:5]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:6]=[C:7]([OH:9])[CH:8]=1

Participants

5

Reactant 2

HCID 25134Boron tribromide2×HCID 3693343HCID 3693343, compound

Product 1

HCID 90102924HCID 90102924, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(3,5-Dimethoxyphenyl)methanesulfonamide (1.7 g, 6.53 mmol) was dissolved in dichloromethane (28 ml). A solution of boron tribromide (1 M in dichloromethane, 33 mL, 33 mmol) was added dropwise and the reaction was stirred at room temperature overnight. Boron tribromide (1M in dichloromethane, 10 ml, 10 mmol) was added and the mixture was stirred for 3 hours. The mixture was diluted with ethyl acetate 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 344 mg (26% yield) of the title compound. Purity 99%.

Workup

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

Sources & evidence

ORD record
ord-1d7896876bd84fefa73dfce1e65e5a62
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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