Water → HCID 69671105, compound

HRID 1191664Notes

Reaction equation

HRID 1191664 reaction equation
[CH2:1]([O:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][C:10]=1[Cl:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Br:23]Br.O>ClCCl>[CH2:1]([O:8][C:9]1[C:10]([Cl:16])=[CH:11][C:12]([NH2:13])=[C:14]([Br:23])[CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 24408BromineHCID 12682854-Benzyloxy-3-chloroaniline

Product 1

HCID 69671105HCID 69671105, compoundYield 125.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-15 °C

Procedure

To a suspension of 4-benzyloxy-3-chloroaniline (674 mg) and potassium carbonate (1.14 g) in dichloromethane (32 mL) was added dropwise a solution of bromine (1.25 g) in dichloromethane (16 mL) at −15° C. in one hour, and the mixture was stirred at −15° C. for 75 minutes. Water was added to the reaction mixture and this resulting mixture was stirred vigorously for additional 10 minutes. The organic layer was separated, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (1.13 g).

Workup

  1. stirringthis resulting mixture was stirred vigorously for additional 10 minutes
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-bff7d43f036a470fa9d6346128e30f1c
Source dataset
uspto-grants-2014_03
Patent number
US08680120B2

Reaction notes

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