2-(Bromomethyl)-1,3-difluorobenzene → HCID 492672, compound

HRID 2182084Notes

Reaction equation

HRID 2182084 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]([O:18][CH3:19])=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=1.[F:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:22]=1[CH2:28]Br>>[F:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:22]=1[CH2:28][N:13]1[C:12]2[CH:14]=[CH:15][CH:16]=[C:17]([O:18][CH3:19])[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 178488935HCID 178488935, compound

Product 1

HCID 492672HCID 492672, compoundYield 91%

Procedure

2-(2,6-Difluorophenyl)-4-methoxylbenzimidazole (5005) (1.25 g, 4.80 mmol) was reacted with 2,6-difluoro-a-bromo-toluene (1.30 g, 6.28 mmol, 130 M %). The crude product was purified by flash chromatography eluting with 2% MeOH/CH2Cl2 and recrystallization from diethylether/hexane (3:1), yielding white crystals of 1-(2,6-difluorobenzyl)-2-(2,6-difluorophenyl)-4-methoxylbenzimidazole (5006) (1.68 g, 4.35 mmol, 91% yield). M.p. 154-155° C. 1H-NMR (200 MHz, CD2Cl2): δ 7.52 (m, 1H, H4′), 7.25 (m, 1H, H4″), 7.19 (dd, J=7.8, 1.0 Hz, 1H, H5), 7.13-7.00 (m, 3H, H3′,5′,6), 6.81 (m, 2H, H3″5″), 6.72 (dd, J=7.8, 1.0 Hz, H7), 5.33 (s, 2H, CH2PhF2), 4.00 (s, 3H, OCH3).

Workup

  1. customThe crude product was purified by flash chromatography
  2. washeluting with 2% MeOH/CH2Cl2 and recrystallization from diethylether/hexane (3:1)

Sources & evidence

ORD record
ord-4ac2b00b9d7d4d7c839332f4e12b2522
Source dataset
uspto-grants-2005_05
Patent number
US06894068B2

Reaction notes

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