Boron tribromide → 2-(4-hydroxyphenyl)-3-methyl-1(2H)-isoquinolinone

HRID 2111842Notes

Reaction equation

HRID 2111842 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:18]([CH3:19])=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:20])=[CH:5][CH:4]=1.B(Br)(Br)Br.C(=O)([O-])O.[Na+]>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:18]([CH3:19])=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:20])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 231511792-(4-methoxyphenyl)-3-methyl-1(2H)-isoquinolinone

Product 1

HCID 231511862-(4-hydroxyphenyl)-3-methyl-1(2H)-isoquinolinoneYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-(4-methoxyphenyl)-3-methyl-1(2H)-isoquinolinone (56 mg, 0.21 mmol) was dissolved in dry methylene chloride, a 1M methylene chloride solution (0.63 mL) of boron tribromide was slowly added at −10° C., and stirred at room temperature for 2 hours. A saturated sodium hydrogen carbonate aqueous solution was added to the reaction mixture, and the methylene chloride distilled off under reduced pressure. 8N hydrochloric acid aqueous solution was added, and the solid precipitate was filtered off and dried to obtain the target compound (48 mg, 91%) as a colorless solid.

Workup

  1. distillationthe methylene chloride distilled off under reduced pressure
  2. addition8N hydrochloric acid aqueous solution was added
  3. filtrationthe solid precipitate was filtered off
  4. customdried

Sources & evidence

ORD record
ord-008e33b9a0394676b190f0ca0d0a9640
Source dataset
uspto-grants-2009_04
Patent number
US07521455B2

Reaction notes

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