Dichloromethane → HCID 24957436, compound

HRID 1522837Notes

Reaction equation

HRID 1522837 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[N:8]([C:14]1[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=1)[CH:7]=[C:6]2[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(Cl)Cl.B(Br)(Br)Br>O>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[N:8]([C:14]1[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=1)[CH:7]=[C:6]2[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 57557431HCID 57557431, compound

Product 1

HCID 24957436HCID 24957436, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-Methoxy-2-(4-methoxyphenyl)-4-phenylisoquinolin-1(2H)-one (0.36 g, 1.01 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 (5.0 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 16 hours. Then, 20 mL of water was added to quench the reaction. The mixture was extracted with ethyl acetate (3×20 mL). The organic layers were 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, 0.29 g, 87.9% yield. MS: 330.2 [M+H]+. 1H NMR (DMSO-d6, 300 MHz): δ 10.31 (s, 1H), 9.69 (s, 1H), 8.19 (d, 1H, J=8.7 Hz), 7.52-7.39 (m, 5H), 7.28 (d, 2H, J=8.7 Hz), 7.18 (s. 1H), 7.00 (dd, 1H, J1=8.7 Hz, J2=2.4 Hz), 6.87-6.82 (m, 3H).

Workup

  1. customfitted with a stirring bar
  2. stirringto stir at room temperature for 16 hours
  3. customto quench
  4. customthe reaction
  5. extractionThe mixture was extracted with ethyl acetate (3×20 mL)
  6. customThe organic layers were separated
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under vacuum
  9. customto give a white solid product, 0.29 g, 87.9% yield

Sources & evidence

ORD record
ord-8b44b72f5b26485c9ce2ee7fc31a8183
Source dataset
uspto-grants-2015_07
Patent number
US09078888B2

Reaction notes

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