2-(Bromomethyl)-1,3-difluorobenzene → HCID 492674, compound

HRID 841532Notes

Reaction equation

HRID 841532 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][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]([CH2:18][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 178435856HCID 178435856, compound

Product 1

HCID 492674HCID 492674, compoundYield 76%

Procedure

2-(2,6-Difluorophenyl)-4-ethylbenzimidazole (4010) (0.70 g, 2.71 mmol) was reacted with 2,6-difluoro-a-bromo-toluene (0.72 g, 3.48 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-ethylbenzimidazole (4011) (0.79 g, 2.06 mmol, 76% yield). M.p. 165-166° C. 1H-NMR (200 MHz, CD2Cl2): δ7.53 (m, 1H, H4′), 7.32 (d, J=8.2 Hz, 1H, H5), 7.29-7.16 (m, 2H, H6,4″), 7.14-7.01 (m, 1H, H7), 7.07 (m, 2H, H3′,5′), 6.81 (m, 2H, H3″,5″), 5.33 (s, 2H, CH2), 3.07 (q, J=7.6 Hz, 2H, CH2), 1.35 (t, J=7.6 Hz, 3H, CH3).

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-846b78a5888c46168dd46e590ddbbf71
Source dataset
uspto-grants-2002_04
Patent number
US06369235B1

Reaction notes

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