Boron tribromide → HCID 59373055, compound

HRID 1471333Notes

Reaction equation

HRID 1471333 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][C:5]2[N:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15]C)[CH:7]=[N:8][C:4]=2[CH:3]=1.B(Br)(Br)Br>ClCCl>[NH2:1][C:2]1[CH:18]=[CH:17][C:5]2[N:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[OH:15])[CH:7]=[N:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 1204110HCID 1204110, compound

Product 1

HCID 59373055HCID 59373055, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5-amino-1-(2-methoxyphenyl)benzimidazole (3) (829 mg, 3.46 mmol), 1.0 M boron tribromide (10 mmol) in dichloromethane (10 mL), and dichloromethane (35 mL) is stirred under argon for 4 h, quenched with sat. NaHCO3 (55 mL), and extracted with ethyl acetate (150 mL, 100 mL, and 50 mL). The extract is washed (brine) and dried. After solvent removal at reduced pressure, the crude material is washed (dichloromethane) to give 604 mg (78%) of 4 as a brown solid, mp 202-203° C. IR 3346, 2956, 1512, 1256 cm−1; 1H NMR (DMSO-d6) δ 5.18 (bs, 2H, NH2), 6.65 (d, J=8.4 Hz, 1H, 6-BenzimidH), 6.90 (s, 1H, 4-BenzimidH), 6.99 (d, J=8.4 Hz, 1H, 7-BenzimidH), 7.02 (d, J=7.8 Hz, 1H, 3-PhH), 7.13 (d, J=7.8 Hz, 1H, 5-ArH), 7.32 (d, J=7.8 Hz, 1H, 4-PhH), 7.38 (d, J=7.8 Hz, 1H, 6-PhH), 8.13 (s, 1H, 2-BenzimidH), 10.15 ppm (s, 1H, OH). HRMS calcd C13H11N3O [M+H]+ 226.0975. found 226.0975.

Workup

  1. customquenched with sat. NaHCO3 (55 mL)
  2. extractionextracted with ethyl acetate (150 mL, 100 mL, and 50 mL)
  3. washThe extract is washed (brine)
  4. customdried
  5. customAfter solvent removal at reduced pressure
  6. washthe crude material is washed (dichloromethane)

Sources & evidence

ORD record
ord-1c2315ae24ad4ecfaa3029cbfe5a0973
Source dataset
uspto-grants-2015_04
Patent number
US09012217B2

Reaction notes

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