Water → HCID 89479694, compound

HRID 589243Notes

Reaction equation

HRID 589243 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([N:6]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[C:7]2[CH:12]=[CH:11][C:10]([O:13]C)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.B(Br)(Br)Br.O>C(Cl)Cl>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([N:6]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 71077150HCID 71077150, compound

Product 1

HCID 89479694HCID 89479694, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-chloro-N-(4-chlorophenyl)-N-(4-methoxyphenyl)aniline (68, 10.79 g, 31.3 mmol) was dissolved in anhydrous DCM (120 mL), and the BBr3 (1.0 M, 38 mL, 37.6 mmol) was added slowly over a period of −20 minutes. The reaction mixture was allowed to stir under an Argon atmosphere for 18 hours. The reaction mixture was slowly poured into water (500 mL) and stirred for 30 minutes. The purple organic layer was separated and the aqueous layer was extracted with DCM (100 mL). The combined organics were washed with water (500 mL), dried over MgSO4, filtered and solvent removed by rotary evaporation. Flash chromatography (15% EtOAc/hexanes) afforded 69 as a clear, light green viscous oil, 9.41 g (91%).

Workup

  1. stirringstirred for 30 minutes
  2. customThe purple organic layer was separated
  3. extractionthe aqueous layer was extracted with DCM (100 mL)
  4. washThe combined organics were washed with water (500 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customsolvent removed by rotary evaporation

Sources & evidence

ORD record
ord-6e12f591b59848019c4a4fad3eeef583
Source dataset
uspto-grants-2016_01
Patent number
US09227986B2

Reaction notes

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