Trimethylsilyl cyanide → 2-(3-Bromophenyl)-2-methoxyethan-1-amine

HRID 1249208Notes

Reaction equation

HRID 1249208 reaction equation
CO[CH:3]([O:11][CH3:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Br:10])[CH:5]=1.C[Si]([C:17]#[N:18])(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>[I-].[Zn+2].[I-].C(#N)C>[CH3:12][O:11][CH:3]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Br:10])[CH:5]=1)[CH2:17][NH2:18]

Participants

6

Reactant 3

HCID 82115Trimethylsilyl cyanideHCID 1053951-Bromo-3-(dimethoxymethyl)benzeneHCID 21226445Aluminium lithium hydride

Product 1

HCID 202252042-(3-Bromophenyl)-2-methoxyethan-1-amine

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 6342AcetonitrileSolvent

Procedure

1-Methoxy-1-(3-bromophenyl)acetonitrile was prepared from 3-bromobenzaldehyde dimethyl acetal and trimethylsilyl cyanide, using zinc iodide as catalyst, by an analogous procedure to that described in Example X1. Reduction of the acetonitrile with lithium aluminium hydride by an analogous procedure to that described in Example X2 gave the title compound.

Sources & evidence

ORD record
ord-9cc7b076408d44caa43e11ed6f07988e
Source dataset
uspto-grants-1986_12
Patent number
US04629737

Reaction notes

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