4-Fluorobenzyl chloride → HCID 13920588, compound

HRID 1761448Notes

Reaction equation

HRID 1761448 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.[Br-].[Na+].[F:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Cl)=[CH:25][CH:24]=1>C1COCC1>[CH3:4][C:2]([NH:5][C:6]([C:8]1[C:13]([CH2:14][CH2:27][C:26]2[CH:29]=[CH:30][C:23]([F:22])=[CH:24][CH:25]=2)=[CH:12][CH:11]=[CH:10][N:9]=1)=[O:7])([CH3:1])[CH3:3]

Participants

6

Reactant 4

HCID 96024-Fluorobenzyl chlorideHCID 253881Sodium BromideHCID 5463796N-tert-Butyl-3-methylpyridine-2-carboxamideHCID 178418339Butyllithium

Product 1

HCID 13920588HCID 13920588, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-5 °C

Procedure

Cool a solution of N-(1,1-dimethylethyl)-3-methyl-2-pyridinecarboxamide (38.4 g, 0.2 mole) in dry THF (250 mL) to -40° C. and add n-butyl lithium (185 mL, 0.44 mole). Add sodium bromide (1.9 g, 18 mmol.) and stir for 15 minutes. Add 4-fluorobenzylchloride (31.8 g. 0.22 mole) and stir for 2.5 hours while warming to -5° C. Quench the reaction with water and extract the product twice with ethyl acetate, then wash with brine (2×). Dry the organic phase over Na2SO4, filter and remove the solvent to give the title compound. (60.0 g, Yield 99%, m.p. 59°-61° C.)

Workup

  1. customQuench
  2. customthe reaction with water
  3. extractionextract the product twice with ethyl acetate
  4. washwash with brine (2×)
  5. dry with materialDry the organic phase over Na2SO4
  6. filtrationfilter
  7. customremove the solvent

Sources & evidence

ORD record
ord-db43820e05d843efaa56176a03d9ef77
Source dataset
uspto-grants-1989_05
Patent number
US04826853

Reaction notes

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