Toluene → HCID 21845804, compound

HRID 619826Notes

Reaction equation

HRID 619826 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1O.[OH-:9].[Na+].Cl[C:12]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][N:13]=1.C1(C)C=CC=CC=1>[Br-].C([P+](CCCC)(CCCC)CCCC)CCCCCCCCCCCCCCC.C(OCC)(=O)C.O>[Cl:18][C:17]1[C:12]([O:9][C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)=[N:13][CH:14]=[CH:15][CH:16]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 72442-BromophenolHCID 14798Sodium HydroxideHCID 169882,3-Dichloropyridine

Product 1

HCID 21845804HCID 21845804, compound

Reagents, catalysts & solvents 3

HCID 84716Hexadecyltributylphosphonium bromideCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Bromophenol (3.74 g, 22 mmol) is stirred with 50% sodium hydroxide solution (16 mL) for about 1 hour then treated with hexadecyltributylphosphonium bromide (3.25 g, 6.4 mmol), 2.3-dichloro-pyridine (3.2 g, 21.6 mmol) and toluene (15 mL). The mixture is heated to 100° C. for 18 hours, cooled and diluted with ethyl acetate and water. The organic layer is separated, washed with dilute NaOH and saturated NaCl, dried (MgSO4) and concentrated. Flash chromatography (5% EtOAc/hexanes) yielded the title compound (4.4 g, 15 mmol).

Workup

  1. temperaturecooled
  2. customThe organic layer is separated
  3. washwashed with dilute NaOH and saturated NaCl
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a908043c8f7641fbb6ec451ab2193eb1
Source dataset
uspto-grants-1999_09
Patent number
US05958918

Reaction notes

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