Carbon tetrabromide → HCID 18956331, compound

HRID 2379900Notes

Reaction equation

HRID 2379900 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[CH:16]([CH3:18])[CH3:17].C(Br)(Br)(Br)[Br:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:20][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[CH:16]([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 18956329HCID 18956329, compound

Product 1

HCID 18956331HCID 18956331, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Part C. A solution of the alcohol prepared in Part B above (4.18 g, 17.0 mmol) and carbon tetrabromide (6.75 g, 20.3 mmol) in methylene chloride (40 mL) was cooled to 0° C., and a solution of triphenylphosphine (5.34 g, 20.4 mmol) in methylene chloride (40 mL) was added dropwise. The mixture was stirred for 20 hours, then evaporated. The residue was separated by flash chromatography (1:2 ethyl acetate-hexane) to afford the product, 1-(5-bromopentyl)-2-(1-methylethyl)-1H-benzimidazole, as an oil (4.80 g, 15.5 mmol, 92%. 1H NMR (CDCl3): 7.79-7.72 (1H, m) ; 7.32-7.21 (3H, m); 4.14 (2H, t, J=7.5 Hz); 3.39 (2H, t, J=6.6 Hz); 3.18 (1H, heptet, J=7.0 Hz); 1.94-1.78 (4H, m); 1.63-1.50 (2H, m); 1.45 (6H, d, J=7.0 Hz).

Workup

  1. customevaporated
  2. customThe residue was separated by flash chromatography (1:2 ethyl acetate-hexane)

Sources & evidence

ORD record
ord-56b2f711baa6493688c9720b93ab0594
Source dataset
uspto-grants-1994_11
Patent number
US05364875

Reaction notes

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