Boron tribromide → HCID 22723459, compound

HRID 1272205Notes

Reaction equation

HRID 1272205 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[S:13][C:12]([S:14]([NH2:17])(=[O:16])=[O:15])=[CH:11][CH:10]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[S:13][C:12]([S:14]([NH2:17])(=[O:16])=[O:15])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22723451HCID 22723451, compound

Product 1

HCID 22723459HCID 22723459, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-75 °C

Procedure

A 70 ml CH2Cl2 suspension of 5-(2-methoxyphenyl)thiophene-2-sulfonamide (1.0 g, 3.7 mmol) is stirred under N2 at −75° C. as boron tribromide (1.1 ml, 12 mmol) is syringed into the reaction mixture. The amber solution is stirred for 30 minutes at −75° C., then at 0° C. for 2–3 hours. The reaction is quenched with ice, extracted with CH2Cl2. The extracts are washed with brine, dried (Na2SO4), filtered, and the filtrate is concentrated. The residue is purified by chromatography (SiO2, ethyl acetate/hexane gradient) to give 720 mg of 5-(2-hydroxyphenyl)thiophene-2-sulfonamide (76%).

Workup

  1. waitat 0° C. for 2–3 hours
  2. customThe reaction is quenched with ice
  3. extractionextracted with CH2Cl2
  4. washThe extracts are washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationthe filtrate is concentrated
  8. customThe residue is purified by chromatography (SiO2, ethyl acetate/hexane gradient)

Sources & evidence

ORD record
ord-93bb5ac861af4fc1a398774bd7833e80
Source dataset
uspto-grants-2007_04
Patent number
US07208505B2

Reaction notes

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