2-(Benzyloxy)-5-bromobenzaldehyde → HCID 4722225, compound

HRID 584995Notes

Reaction equation

HRID 584995 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][C:10]=1[CH:11]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.CN.[C:21]([BH3-])#[N:22].[Na+]>>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][C:10]=1[CH2:11][NH:22][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 7330872-(Benzyloxy)-5-bromobenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochloride

Product 1

HCID 4722225HCID 4722225, compound

Procedure

In a manner similar to that of Example 75(b), by reacting 22.5 g (77 mmol) of 2-benzyloxy-5-bromobenzaldehyde, 26.1 g (386 mmol) of methylamine hydrochloride and 7.3 g (116 mmol) of sodium cyanoborohydride, and after purification by chromatography on a column of silica eluted with a dichloromethane/methanol mixture (9/1) and 0.5% isopropylamine, 12.2 g (51%) of the expected product are obtained in the form of a pale yellow oil.

Workup

  1. customafter purification by chromatography on a column of silica
  2. washeluted with a dichloromethane/methanol mixture (9/1) and 0.5% isopropylamine, 12.2 g (51%) of the expected product
  3. customare obtained in the form of a pale yellow oil

Sources & evidence

ORD record
ord-5269bcc013af439b92b9f196d8aefa7e
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

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