2-(Bromomethyl)-1,3-difluorobenzene → HCID 22482465, compound

HRID 841535Notes

Reaction equation

HRID 841535 reaction equation
[CH:1]1([C:4]2[NH:5][C:6]3[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[CH:9][C:7]=3[N:8]=2)[CH2:3][CH2:2]1.[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[C:17]=1[CH2:23]Br>>[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[C:17]=1[CH2:23][N:8]1[C:7]2[CH:9]=[CH:10][CH:11]=[C:12]([O:13][CH3:14])[C:6]=2[N:5]=[C:4]1[CH:1]1[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 5814352-(Bromomethyl)-1,3-difluorobenzeneHCID 178488921HCID 178488921, compound

Product 1

HCID 22482465HCID 22482465, compoundYield 92.1%

Procedure

2-(Cyclopropyl)-4-methoxylbenzimidazole (1.00 g, 5.32 mmol) (5014) 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% methanol/CH2Cl2 and recrystallization from diethylether/hexane (3:1), yielding white crystals of 1-(2,6-Difluorobenzyl)-2-(cyclopropyl)-4-methoxylbenzimidazole (5016) (1.54 g, 4.90 mmol, 92% yield). M.p. 136-139° C. 1H-NMR (200 MHz, CD2Cl2) δ7.31 (m, 1H, H4′), 7.07 (dd, J=8.0, 7.8 Hz, 1H, H6), 6.94 (m, 3H, H3′,5′,5), 6.61 (dd, J=7.8, 1.0 Hz, H7), 5.46 (s, 2H, CH2PhF2), 3.95 (s, 3H, OCH3), 2.20-2.03 (m, 1H), 1.18-0.97 (m, 4H).

Workup

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

Sources & evidence

ORD record
ord-cefdfd3737004e55877c171326a3052b
Source dataset
uspto-grants-2002_04
Patent number
US06369235B1

Reaction notes

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