Bromide ion → HCID 117856852, compound

HRID 509918Notes

Reaction equation

[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]=O)=[CH:5][CH:4]=1.C(C=P([C:30]1[CH:35]=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(OCC)=O.[OH-].[Na+].[H-].[H-].[H-].[H-].[Li+].[Al+3].[Br-].[Br:45]N1C(=O)CCC1=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>>[Br:45][CH2:35][CH2:30][CH2:9][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[N:8][CH:7]=1

Participants

Reactant 7

HCID 259Bromide ion

HCID 11776Triphenylphosphine

HCID 14798Sodium Hydroxide

HCID 67184N-bromobutanimide

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester

HCID 33645766-Methoxypyridine-3-carbaldehyde

HCID 21226445Aluminium lithium hydride

Product 1

HCID 117856852HCID 117856852, compound

Procedure

The title compound is prepared from 6-methoxy-3-pyridinecarboxaldehyde (0.5 g, Aldrich) by a sequence of standard transformations consisting of Wittig reaction with (carbethoxymethylene)triphenylphosphorane and NaOH, catalytic hydrogenation of the exocyclic C—C double bond, reduction to the corresponding alcohol with LiAlH4, and conversion to the bromide using N-bromosuccinimide and PPh3.

Sources & evidence

ORD record: ord-0cc5c2990a0f4943bf1e3d61d58e5a19
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096548B2

Reaction notes

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