Carbon tetrabromide → HCID 89553810, compound

HRID 590386Notes

Reaction equation

HRID 590386 reaction equation
O[CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([CH:14]=[O:15])=[CH:13][C:8]=2[NH:7][C:6]1=[O:16].C(Br)(Br)(Br)[Br:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:18][CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([CH:14]=[O:15])=[CH:13][C:8]=2[NH:7][C:6]1=[O:16]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 89553803HCID 89553803, compound2×

Product 1

HCID 89553810HCID 89553810, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1185 mg (5.38 mmol) of 1-(3-hydroxypropyl)-2-oxo-2,3-dihydro-1H-benzimidazole-5-carbaldehyde (Intermediate 14) are suspended in 56 ml of dichloromethane. 2285 mg (6.89 mmol) of carbon tetrabromide and then 6890 mg of polymer-supported triphenyl phosphine (1 mmol/g; 6.89 mmol) are added. The mixture is shaken at rt for 24 hr. The polymer is filtered and sequentially washed with dichloromethane, EtOH and MeOH. The filtrates are concentrated and the residue (2.2 g) is chromatographically purified over silicagel eluting with chloroform/EtOH (100/0 to 90/10). 0.3 g of pure title compound are obtained (20% yield).

Workup

  1. filtrationThe polymer is filtered
  2. washsequentially washed with dichloromethane, EtOH and MeOH
  3. concentrationThe filtrates are concentrated
  4. customthe residue (2.2 g) is chromatographically purified over silicagel
  5. washeluting with chloroform/EtOH (100/0 to 90/10)

Sources & evidence

ORD record
ord-2d887eff13aa4086b3f9ba7805f25b20
Source dataset
uspto-grants-2016_01
Patent number
US09233108B2

Reaction notes

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