Dichloromethane → HCID 135979344, compound

HRID 1694529Notes

Reaction equation

HRID 1694529 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 to 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. concentrationto concentrated
  4. customThe residue is recrystallized from hexane/benzene

Sources & evidence

ORD record
ord-3f982ad8b6704dba933cacc267092c0e
Source dataset
uspto-grants-2012_04
Patent number
US08158733B2

Reaction notes

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