3-BROMO-7-METHOXY-1-NAPHTHONITRILE synthesis

6synthesis methods

Product Name:3-BROMO-7-METHOXY-1-NAPHTHONITRILE
CAS Number:847505-83-3
Molecular formula:C12H8BrNO
Molecular Weight:262.1

1-Naphthalenecarbonitrile, 3,8-dibromo-7-methoxy-

847505-82-2
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847505-83-3
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Yield:847505-83-3 73%

Reaction Conditions:

with hydrogenchloride;acetic acid;tin(ll) chloride in water at 100; for 6 h;

Steps:

1; 3 3-BROMO-7-METHOXY-1-NAPHTHONITRILE

EXAMPLE 3 3-BROMO-7-METHOXY-1-NAPHTHONITRILE To slurry of 3,8-dibromo-7-methoxy-1-naphthonitrile (1.62 kg) and Tin (II) chloride dihydrate (1.24 kg, 5.50 mol) in acetic acid (5 L) is added conc. HCl (37% wt, 2.50 L) through a dropping funnel at 100° C. during a period of 2 h. The mixture is stirred at 100° C. for 4 h. Then, the mixture is cooled to room temperature. The solid is filtered, washed with 1% wt HCl (2*1.00 L), water (1.00 L) and dried to give the title compound as a white solid (524 g, 73%). ¹H NMR (CDCl₃): δ8.13 (d, 1 H, J=1.8 Hz), 7.93 (d, 1 H, J=1.9 Hz), 7.72 (d, 1 H, J=9.0 Hz),7.41 (d, 1 H, J=2.4 Hz), 7.28 (dd, 1 H, J=2.4 Hz, 9.0 Hz), 3.99 (s, 3H).

References:

US2005/54870,2005,A1 Location in patent:Page/Page column 3; 5; 7

158365-54-9 Synthesis