Dichloromethane → HCID 135979344, compound

HRID 1689830Notes

Reaction equation

HRID 1689830 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[C:16]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:15]=[C:14]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:13]=1[O:26]C)[CH:8]=[CH:7]2.B(Br)(Br)Br.C(Cl)Cl>O>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[C:16]([C:18]([CH3:19])([CH3:20])[CH3:21])[CH:15]=[C:14]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:13]=1[OH:26])[CH:8]=[CH:7]2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 58114887HCID 58114887, compound

Product 1

HCID 135979344HCID 135979344, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 8-bromo-2-(3,5-di-tert-butyl-2-methoxyphenyl)quinoline (4.89 g, 11.5 mmol), BBr3 (1.63 mL, 18 mmol), and CH2Cl2 (50 mL) is stirred for 4 h at 20° C. The reaction mixture is then diluted with cold water (100 mL). The organic phase is separated, washed with water and brine, and then concentrated. The residue is recrystallized from hexane/benzene. Yield: 3.3 g (70%).

Workup

  1. customThe organic phase is separated
  2. washwashed with water and brine
  3. concentrationconcentrated
  4. customThe residue is recrystallized from hexane/benzene

Sources & evidence

ORD record
ord-421b4e8b3cc947f1b87a76af9ff20243
Source dataset
uspto-grants-2012_04
Patent number
US08153544B2

Reaction notes

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