Carbon tetrabromide → 1-(2-Bromoethyl)-6-methoxy-1H-benzo[d]imidazole

HRID 624058Notes

Reaction equation

HRID 624058 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[CH:9][N:8]([CH2:11][CH2:12]O)[C:7]=2[CH:14]=1.C(Br)(Br)(Br)[Br:16].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[Br:16][CH2:12][CH2:11][N:8]1[C:7]2[CH:14]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=2[N:10]=[CH:9]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 450778812-(6-methoxy-1H-benzo[d]imidazol-1-yl)ethanol

Product 1

HCID 682836201-(2-Bromoethyl)-6-methoxy-1H-benzo[d]imidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(6-methoxy-1H-benzo[d]imidazol-1-yl)ethanol (200 mg, 1.04 mmol) in DCM (6.0 mL), CBr4 (397 mg, 1.20 mmol) was added, then the reaction mixture was cooled to 0° C. and PPh3 (314 mg, 1.20 mmol) was added. After stirring at rt for 2 h the solvent was removed under reduced pressure to yield the title compound as a brown oil, which was used us such in the next step. LC-MS conditions B: tR=0.42 min, [M(79Br)+H]+=255.08.

Workup

  1. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-9acd4a9b097342f087e06c046794a06a
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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