Dichloromethane → HCID 24961485, compound

HRID 1522827Notes

Reaction equation

HRID 1522827 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12]C)[CH:10]=2)[C:5](=[O:14])[N:4]([C:15]2[CH:20]=[CH:19][C:18]([O:21]C)=[CH:17][CH:16]=2)[CH:3]=1.C(Cl)Cl.B(Br)(Br)Br>O>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[C:5](=[O:14])[N:4]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 24962933HCID 24962933, compound

Product 1

HCID 24961485HCID 24961485, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Bromo-6-methoxy-2-(4-methoxyphenyl)isoquinolin-1(2H)-one (0.22 g, 0.61 mmol) was placed in a dry 150 mL single-necked flask fitted with a stirring bar and septa. Methylene chloride (30 mL) was added via a syringe. Boron tribromide (1.83 mL of 1.0 M methylene chloride solution) was added dropwise with stirring under argon atmosphere at room temperature. The reaction mixture was allowed to stir at room temperature for 20 hours. Then, 20 mL of water was added to quench the reaction. The mixture was extracted with 50 mL of ethyl acetate. The organic layer was separated, dried over anhydrous magnesium sulfate and concentrated under vacuum. The residue was subjected to flash column chromatography (silica gel, CH2Cl2/MeOH=9/1 v/v) to give a white solid product, 0.10 g, 49.4% yield. MS: 334.2 [M+H]+. 1H NMR (DMSO-d6, 300 MHz): δ 10.58 (s, 1H), 9.83 (s, 1H), 8.12 (d, 1H, J=8.7 Hz), 7.71 (s, 1H), 7.22 (d, 2H, J=8.7 Hz), 7.09 (d, 1H, J=21. Hz), 7.04 (dd, 1H, J1=8.7 Hz, J2=2.4 Hz), 6.84 (d, 2H, J=8.7 Hz).

Workup

  1. customfitted with a stirring bar
  2. stirringto stir at room temperature for 20 hours
  3. customto quench
  4. customthe reaction
  5. extractionThe mixture was extracted with 50 mL of ethyl acetate
  6. customThe organic layer was separated
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under vacuum
  9. customto give a white solid product, 0.10 g, 49.4% yield

Sources & evidence

ORD record
ord-64a4983818674db689cfb7d2a90f26dd
Source dataset
uspto-grants-2015_07
Patent number
US09078888B2

Reaction notes

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