3-Fluorobenzyl chloride → HCID 18951200, compound

HRID 2253865Notes

Reaction equation

HRID 2253865 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.Cl[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[F:18][C:14]1[CH:13]=[C:12]([CH2:11][N:1]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=[N:2]2)[CH:17]=[CH:16][CH:15]=1.[F:18][C:14]1[CH:13]=[C:12]([CH2:11][N:2]2[N:3]=[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]3=[N:1]2)[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 99743-Fluorobenzyl chlorideHCID 11430Potassium CarbonateHCID 178418385HCID 178418385, compound

Product 2

HCID 18951200HCID 18951200, compoundHCID 18951204HCID 18951204, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a procedure as in Example 2 but using 1H-benzotriazole (20.6 g, 0.173 mol), 1-(chloromethyl)-3-fluorobenzene (25.0 g, 0.173 mol), K2CO3 (35.9 g) and CH3CN (150 mL) for 1 h gave the title compound and (3-fluorophenyl)methyl-2H-benzotriazole. Similar workup and recrystallization gave the pure 1H-isomer (73%): mp 103°-104° C. (cyclohexane); 1H NMR (270 MHz, CDCl3) δ 5.87 (s, 2H, CH2), 6.97-7.08 (m, 3H), 7.29-7.49 (m, 4H), 8.10 (d, J=8.0 Hz, 1H); Anal. Calcd for C13H10N3F (227.24): C, 68.71; H, 4.44; Found: C, 68.40; H, 4.67.

Workup

  1. customfor 1 h

Sources & evidence

ORD record
ord-1bd9bd370b364b418059177c8f1bfed2
Source dataset
uspto-grants-1993_08
Patent number
US05233046

Reaction notes

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