Carbon tetrabromide → HCID 86672640, compound

HRID 1616356Notes

Reaction equation

HRID 1616356 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18]O)=[CH:14][CH:13]=2)[N:11]=1)[C:5]([O:7][CH3:8])=[O:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:40]>C(Cl)Cl>[Br:40][CH2:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[CH:9]=[C:4]([CH:3]=[C:2]([Cl:1])[N:11]=2)[C:5]([O:7][CH3:8])=[O:6])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 86672641HCID 86672641, compound

Product 1

HCID 86672640HCID 86672640, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-chloro-6-(4-(hydroxymethyl)phenyl)isonicotinate (0.67 g, 2.418 mmol) in DCM (10 mL), triphenyl phosphine (1 g, 3.86 mmol) and carbon tetrabromide (1.63 g, 3.87 mmol) were added at 0° C. and reaction mass stirred for overnight at rt. On completion, reaction mass was concentrated and purified by column chromatography over silica gel affording methyl 2-(4-(bromomethyl)phenyl)-6-chloroisonicotinate (0.53 g, 64%).

Workup

  1. customreaction mass
  2. customOn completion, reaction mass
  3. concentrationwas concentrated
  4. custompurified by column chromatography over silica gel

Sources & evidence

ORD record
ord-36a0e3748174416b9e0239034794aba9
Source dataset
uspto-grants-2014_07
Patent number
US08765732B2

Reaction notes

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