4-Fluorobenzyl chloride → HCID 13920588, compound

HRID 542764Notes

Reaction equation

HRID 542764 reaction equation
[CH3:1][C:2]([NH:5][C:6]([C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][N:9]=1)=[O:7])([CH3:4])[CH3:3].C([Li])CCC.[F:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Cl)=[CH:23][CH:22]=1>C1COCC1.[Br-].[Na+]>[CH3:4][C:2]([NH:5][C:6]([C:8]1[C:13]([CH2:14][CH2:25][C:24]2[CH:27]=[CH:28][C:21]([F:20])=[CH:22][CH:23]=2)=[CH:12][CH:11]=[CH:10][N:9]=1)=[O:7])([CH3:1])[CH3:3]

Participants

6

Reactant 3

HCID 96024-Fluorobenzyl chlorideHCID 5463796N-tert-Butyl-3-methylpyridine-2-carboxamideHCID 178418339Butyllithium

Product 1

HCID 13920588HCID 13920588, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 253881Sodium BromideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-5 °C

Procedure

To a cooled (-40° C.) solution of N-(1,1-dimethylethyl)-3-methyl-2-pyridinecarboxamide (38.4 g, 0.2 mole) in dry THF (250 mL) is added n-butyl lithium (185 mL, 0.44 mole). Then sodium bromide (1.9 g, 18 mmol.) is added and is allowed to stir for 15 minutes. 4-Fluorobenzylchloride (31.8 g. 0.22 mole) was added and the reaction is allowed to stir for 21/2 hours while warming up to -5° C. The reaction is then quenched with water and the product is extracted twice with ethyl acetate followed by washing twice with brine. The organic phase is dried over Na2SO4, filtered and solvent is removed to give desired compound (60.0 g) in 99% yield, m.p. 59°-61° C.

Workup

  1. stirringto stir for 21/2 hours
  2. customThe reaction is then quenched with water
  3. extractionthe product is extracted twice with ethyl acetate
  4. washby washing twice with brine
  5. dry with materialThe organic phase is dried over Na2SO4
  6. filtrationfiltered
  7. customsolvent is removed

Sources & evidence

ORD record
ord-60b5bdff122d421c98b2cdd091e4bcc5
Source dataset
uspto-grants-1987_04
Patent number
US04659716

Reaction notes

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