4-Fluorobenzyl chloride → 1-[(4-fluorophenyl)methyl]benzotriazole

HRID 2253864Notes

Reaction equation

HRID 2253864 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][C:15]([F:18])=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[F:18][C:15]1[CH:16]=[CH:17][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:13][CH:14]=1.[F:18][C:15]1[CH:16]=[CH:17][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:13][CH:14]=1

Participants

6

Reactant 3

HCID 96024-Fluorobenzyl chlorideHCID 11430Potassium CarbonateHCID 178418385HCID 178418385, compound

Product 2

HCID 7336221-[(4-fluorophenyl)methyl]benzotriazoleHCID 3746541HCID 3746541, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a procedure as in Example 2 but using 1H-benzotriazole (23.8 g, 0.200 mol), 1-(chloromethyl)-4-fluorobenzene (29.0 g, 0.200 mol) and K2CO3 (70 g) in CH3CN (300 mL) for 1 hour gave the title compound and (4-fluorophenyl)methyl-2H-benzotriazole. Workup and recrystallization gave the mixture of the 1H and 2H-isomers (75% yield) which was used in the subsequent reactions. A sample (5 g) was chromatographed (PE/EtOAc 9:1) eluting first the 2H isomer and then the title compound: mp 92°-94° C. (cyclohexane); 1H NMR (300 MHz, CDCl3) δ 5.82 (s, 2H, CH2), 7.00-7.06 (m, 2H), 7.25-7.46 (m, 5H), 8.08 (d, J=8.9 Hz, 1H); IR (CDCl3) 3052 (w), 2938 (w), 1609, 1513, 1451 (w), 1351 (w), 1315 (w), 1269 (w), 1230 (s), 1159, 1084 cm-1. MS (EI) m/e 227 (M+, 52.6), 198 (100), 109 (96.9); Anal. Calcd or C13H10N3F (227.24): C, 68.71; H, 4.44; F, 8.36; N, 18.49; Found: C, 68.44; H, 4.44; F, 8.40; N, 18.57.

Workup

  1. customfor 1 hour

Sources & evidence

ORD record
ord-828aa2d27bbd4f7199eff7de7f06bbe0
Source dataset
uspto-grants-1993_08
Patent number
US05233046

Reaction notes

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