2-Methoxyaniline → 4-Bromo-2-methoxyaniline

HRID 611545

Reaction equation

HRID 611545 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].[Br:10]C1C(=O)C(Br)=CC(Br)(Br)C=1>>[Br:10][C:8]1[CH:7]=[CH:6][C:4]([NH2:5])=[C:3]([O:2][CH3:1])[CH:9]=1

Participants

3

Reactant 2

HCID 70002-MethoxyanilineHCID 884332,4,4,6-Tetrabromocyclohexa-2,5-dienone

Product 1

HCID 4592574-Bromo-2-methoxyaniline

Procedure

2-Methoxyaniline was brominated with 2,4,4,6-tetrabromo-2,5-cyclohexadien-1-one to give 4-bromo-2-methoxyaniline which was reacted with di-tert-butyldicarbonate in tetrahydrofuran to protect the amine group. The product was treated with butyllithium at -78° C. and then with trimethyltin chloride to give 4-tert-butoxycarbonylamino-3-methoxyphenyl trimethyl stannane.

Sources & evidence

ORD record
ord-81be778add174383838e4f6b692fb180
Source dataset
uspto-grants-1999_12
Patent number
US06001839

Linked notes

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