2-Methyl-4-methoxyaniline → HCID 67402403, compound

HRID 913858Notes

Reaction equation

HRID 913858 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[C:5]([CH3:10])[CH:4]=1.[Br:11]Br>C(Cl)(Cl)Cl>[BrH:11].[Br:11][C:8]1[CH:9]=[C:3]([O:2][CH3:1])[CH:4]=[C:5]([CH3:10])[C:6]=1[NH2:7]

Participants

4

Reactant 2

HCID 76102-Methyl-4-methoxyanilineHCID 24408Bromine

Product 1

HCID 67402403HCID 67402403, compoundYield 170.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

4-Methoxy-2-methylaniline (9.30 ml, 72.9 mmol) in chloroform (250 ml ) at 0° C. was added a solution of bromine (3.76 ml, 72.9 mmol) in chloroform (60 ml) dropwise over ca. 3 h. The reaction mixture was concentrated, diluted with dichloromethane and concentrated, diluted again with diethyl ether and concentrated, and dried under high vacuum to give 18.5 g of 2-bromo-4-methoxy-6-methylaniline hydrobromide (85%). LC/MS (HPLC method 3): tR=1.395 min, 216.03(MH)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with dichloromethane
  3. concentrationconcentrated
  4. additiondiluted again with diethyl ether
  5. concentrationconcentrated
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-a4341896da464573bd5550f6262f553a
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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