Boron tribromide → HCID 135433621, compound

HRID 991004Notes

Reaction equation

HRID 991004 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:14]3[S:20][C:19]4[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=4[C:15]=3[NH:16][N:17]=2)=[CH:9][CH:8]=1>ClCCl>[OH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[C:14]3[S:20][C:19]4[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=4[C:15]=3[NH:16][N:17]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 18415861HCID 18415861, compound

Product 1

HCID 135433621HCID 135433621, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Boron tribromide (3.0 ml of a 1.0M solution in dichloromethane) was added to a solution of the product from Example 60 (210 mg) in dichloromethane (10 ml) at −78° C. under nitrogen with stirring. The mixture was allowed to warm to ambient temperature slowly, and after stirring at this temperature for 2 days the mixture was quenched by the addition of aqueous ammonium chloride solution. The organic layer was separated, dried and evaporated to give a residue which was purified by flash column chromatography on silica using dichloromethane and then increasing amounts of methanol, up to 15% of methanol, in dichloromethane as the mobile phase. Appropriate fractions were collected, combined and evaporated to give 3-(4-hydroxyphenyl)-1H-[1]benzothieno[3,2-c]pyrazole, m.p. 137-1 39° C.

Workup

  1. stirringafter stirring at this temperature for 2 days the mixture
  2. customwas quenched by the addition of aqueous ammonium chloride solution
  3. customThe organic layer was separated
  4. customdried
  5. customevaporated
  6. customto give a residue which
  7. customwas purified by flash column chromatography on silica
  8. customAppropriate fractions were collected
  9. customevaporated

Sources & evidence

ORD record
ord-42f080fa32ce484987a8e2298565daf2
Source dataset
uspto-grants-2002_10
Patent number
US06462036B1

Reaction notes

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