Boron tribromide → HCID 23062636, compound

HRID 491823Notes

Reaction equation

HRID 491823 reaction equation
[C:1]([C:3]1[CH:20]=[C:19]([O:21]C)[CH:18]=[CH:17][C:4]=1[O:5][CH2:6][C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=1)=[O:8])#[N:2].B(Br)(Br)Br>ClCCl>[C:1]([C:3]1[CH:20]=[C:19]([OH:21])[CH:18]=[CH:17][C:4]=1[O:5][CH2:6][C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=1)=[O:8])#[N:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 23062710HCID 23062710, compound

Product 1

HCID 23062636HCID 23062636, compoundYield 44.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the suspension of (2-cyano-4-methoxyphenoxy)-N-(5-chloropyridin-2-yl)acetamide (40.0 g) obtained in Reference Example 59 in dichloromethane (2000 ml), boron tribromide (173 g) is added at −58° C. dropwise over 40 minutes. The reaction solution is stirred for 26 hours with keeping the internal temperature between −20° C. and 0° C., and then poured to an ice-water. The precipitated solid is collected by filtration, washed with water, and then dried under reduced pressure. A part of the resulting solid (37.2 g), i.e. 24.3 g thereof is purified by silica gel column chromatography (eluent: chloroform/methanol=50/1-10/1) to give the title compound (17.0 g).

Workup

  1. customthe internal temperature between −20° C. and 0° C.
  2. filtrationThe precipitated solid is collected by filtration
  3. washwashed with water
  4. customdried under reduced pressure
  5. customA part of the resulting solid (37.2 g), i.e. 24.3 g thereof is purified by silica gel column chromatography (eluent: chloroform/methanol=50/1-10/1)

Sources & evidence

ORD record
ord-0b65c423e3544fcb83724a893ad8bc5a
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

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