ChemicalBook CAS DataBase List 4-BROMO-3-METHOXYANILINE

4-BROMO-3-METHOXYANILINE synthesis

11synthesis methods

Product Name:4-BROMO-3-METHOXYANILINE
CAS Number:19056-40-7
Molecular formula:C7H8BrNO
Molecular Weight:202.05

77337-82-7 Synthesis

77337-82-7
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19056-40-7
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Yield:19056-40-7 89%

Reaction Conditions:

aluminum nickel in methanol;hexane;ethyl acetate

Steps:

1 5-(4-Bromo-3-methoxyphenyl)-N-hydroxy-2-furancarboximidamide Hydrochloride STR4
EXAMPLE 1 5-(4-Bromo-3-methoxyphenyl)-N-hydroxy-2-furancarboximidamide Hydrochloride STR4 2-Bromo-5-nitroanisole (25 g, 0.116 mole) (Fairfield Chemical Co., Blythewood, S.C.) was dissolved in 150 ml of 70:30 methanol/ethyl acetate. Raney nickel (1.0 g) was added to the solution. The mixture was hydrogenated on a Parr shaker for 3 hours, then filtered through Celite. The dark brown filtrate was treated with Darco and concentrated under reduced pressure to a brown solid. The solid was dissolved in 50:50 ethyl acetate/hexane (1 L) and filtered through a 2-inch cake of silica gel (column grade). The resulting solution was concentrated under reduced pressure to a solid yielding 19.3 g (89% yield) of 4-bromo-3-anisidine (O).

References:

Norwich Eaton Pharmaceuticals, Inc. US4882354, 1989, A

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536-90-3 Synthesis