Boron tribromide → HCID 23062636, compound

HRID 1820933Notes

Reaction equation

HRID 1820933 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 a suspension of (2-cyano-4-methoxyphenoxy)-N-(5-chloropyridin-2-yl)acetamide (40.0 g) obtained in Reference Example 65 in dichloromethane (2000 ml) is added dropwise boron tribromide (173 g) at −58° C. over 40 minutes. The reaction solution is stirred for 26 hours while keeping the internal temperature between −20° C. and 0° C., and then poured to ice-water. The precipitated solids are collected by filtration, washed with water, and dried under reduced pressure. A portion (24.3 g) of the resulting solids (37.2 g) are purified by silica gel column chromatography (eluent: chloroform/methanol=50/1-10/1) to give the title compound (17.0 g). APCI-MS M/Z:304/306[M+H]+

Workup

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

Sources & evidence

ORD record
ord-5d3a7101d5194d63976d9303f3e95012
Source dataset
uspto-grants-2009_10
Patent number
US07605158B2

Reaction notes

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