Dichloromethane → 1353777-30-6

HRID 1470738Notes

Reaction equation

HRID 1470738 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([NH2:9])=[C:4]([O:10][CH3:11])[CH:3]=1.B(Br)(Br)Br.Cl[CH2:17]Cl>>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]2[N:9]=[C:11]([CH3:17])[O:10][C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 6344Dichloromethane2×HCID 25134Boron tribromideHCID 106802184-Bromo-2-methoxy-6-methylaniline

Product 1

HCID 679709581353777-30-6

Procedure

0.50 g (2.31 mmol) 4-Bromo-2-methoxy-6-methyl-phenylamine in 5 mL dichloromethane is cooled with ice/ethanol and 0.24 mL (2.49 mmol) boron tribromide in 5 mL dichloromethane is added slowly. Stirring is continued for 30 under cooling and 2 h at rt. The mixture is poured onto ice, allowed to stand for 30 min and the aq. layer is extracted with dichloromethane. The aq. phase is treated with NaHCO3 until the mixture shows basic pH, followed by extraction with dichloromethane. The combined organic phases are dried and concentrated to yield the desired product which is used without further purification.

Workup

  1. additionis added slowly
  2. additionThe mixture is poured onto ice
  3. extractionthe aq. layer is extracted with dichloromethane
  4. additionThe aq. phase is treated with NaHCO3 until the mixture
  5. extractionfollowed by extraction with dichloromethane
  6. customThe combined organic phases are dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f9dddfb9c2a74a6e90870c2d0393c016
Source dataset
uspto-grants-2015_04
Patent number
US09006450B2

Reaction notes

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