2-(Bromomethyl)-1,3-difluorobenzene → HCID 22482478, compound

HRID 841546Notes

Reaction equation

HRID 841546 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[NH:10][C:11]2[C:17]([CH2:18][O:19][C:20](=[O:22])[CH3:21])=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=1.[F:23][C:24]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:25]=1[CH2:26]Br>>[F:23][C:24]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:25]=1[CH2:26][N:13]1[C:12]2[CH:14]=[CH:15][CH:16]=[C:17]([CH2:18][O:19][C:20](=[O:22])[CH3:21])[C:11]=2[N:10]=[C:9]1[C:3]1[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=1[F:1]

Participants

3

Reactant 2

HCID 5814352-(Bromomethyl)-1,3-difluorobenzeneHCID 178475829HCID 178475829, compound

Product 1

HCID 22482478HCID 22482478, compoundYield 118.4%

Procedure

2-(2,6-Difluorophenyl)4-acetoxymethylbenzimidazole (Example 101) (3.55 g, 11.74 mmol) and 2,6-difluorobenzylbromide (3.40 g, 16.4 mmol, 140 M%) were reacted. The crude product was purified using flash chromatography eluting with 2% methanol/CH2Cl2 and recrystallization from diethylether, yielding white crystals of 1-(2,6-difluorobenzyl)-2-(2,6-difluorophenyl)-4-acetoxymethylbenzimidazole (5.94 g, 13.9 mmol, 76% yield). M.p. 126-127° C. 1HNMR (300 MHz, CD2Cl2): δ7.54 (m, 1H, H4′), 7.48 (m, 1H, H6), 7.33-7.27 (m, 2H, H5,7), 7.25 (m, 1H, H″), 7.08 (m, 2H, H3′,5′), 6.82 (m, 2H, H3″,5″), 5.54 (s, 2H, CH2PhF2), 5.36 )s, 2H, CH2O), 2.08 (s, 3H, OAc).

Workup

  1. customThe crude product was purified
  2. washeluting with 2% methanol/CH2Cl2 and recrystallization from diethylether

Sources & evidence

ORD record
ord-3d869a02fab34fffa91c79eaa4fed3ed
Source dataset
uspto-grants-2002_04
Patent number
US06369235B1

Reaction notes

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