Carbon tetrabromide → HCID 12992882, compound

HRID 901054Notes

Reaction equation

HRID 901054 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:3]=1[C:4]([N:6]([C:15](=[O:24])[C:16]1[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:23])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13]O)=[CH:9][N:8]=1)=[O:5].C(Br)(Br)(Br)[Br:31].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])O.[Na+]>ClCCl>[Cl:1][C:2]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:3]=1[C:4]([N:6]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][Br:31])=[CH:9][N:8]=1)[C:15](=[O:24])[C:16]1[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:23])=[O:5]

Participants

6

Reactant 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 12992881HCID 12992881, compound

Product 1

HCID 12992882HCID 12992882, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 40 ml of dichloromethane was dissolved 855 mg (1.8 mmol) of 2,6-dichloro-N-(2,6-dichlorobenzoyl)-N-(5-hydroxymethylpyrid-2-yl)benzamide (e), and 905 mg (2.7 mmol) of carbon tetrabromide and 573 mg (2.2 mmol) of triphenylphosphine were added. The mixture was stirred for 2.5 hours, and treated with a saturated sodium hydrogen carbonate aqueous solution. The mixture was subjected to extraction with chloroform, and the extract was washed with a saturated sodium chloride aqueous solution. The solvent was evaporated off under vacuum, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate (volume ratio)=3:1-2:1) to give 631 mg (yield 65%) of 2,6-dichloro-N-(5-bromomethylpyrid-2-yl)-N-(2,6-dichlorobenzoyl)benzamide (f).

Workup

  1. additionwere added
  2. extractionThe mixture was subjected to extraction with chloroform
  3. washthe extract was washed with a saturated sodium chloride aqueous solution
  4. customThe solvent was evaporated off under vacuum
  5. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate (volume ratio)=3:1-2:1)

Sources & evidence

ORD record
ord-aa0e4a09f18a424d881771e20a8d75c3
Source dataset
uspto-grants-2008_04
Patent number
US07361679B2

Reaction notes

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