Boron tribromide → HCID 178497566, compound

HRID 579460Notes

Reaction equation

HRID 579460 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:14][C:13]3[C:15]([CH:21]=[O:22])=[C:16]([O:19]C)[CH:17]=[CH:18][C:12]=3[N:11]=2)=[CH:6][CH:5]=1.B(Br)(Br)Br>ClCCl>[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:5]=[CH:6][C:7]([C:10]2[NH:14][C:13]3[C:15]([CH:21]=[O:22])=[C:16]([OH:19])[CH:17]=[CH:18][C:12]=3[N:11]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 178497565HCID 178497565, compound

Product 1

HCID 178497566HCID 178497566, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 4-(7-Formyl-6-methoxy-1H-benzoimidazol-2-yl)-benzoic acid methyl ester (650 mg, 2.1 mmol) in abs. dichloromethane (30 mL) at −78° C., boron tribromide (1.20 mL, 3.20 g, 12.60 mmol) was added dropwise and the mixture was stirred for 1 h, then overnight at room temperature. The yellow suspension was cooled to −78° C. and quenched with methanol (30 mL) followed by evaporation. The residue was partitioned between saturated sodium bicarbonate (30 mL) and chloroform (30 mL). The organic phase was dried (Na2SO4) and evaporated. The title compound (360 mg, 1.22 mmol, 58%) was isolated as a light green solid.

Workup

  1. customovernight
  2. customat room temperature
  3. customquenched with methanol (30 mL)
  4. customfollowed by evaporation
  5. customThe residue was partitioned between saturated sodium bicarbonate (30 mL) and chloroform (30 mL)
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. customevaporated

Sources & evidence

ORD record
ord-541ca7386de7435fbf642580f5576adf
Source dataset
uspto-grants-2015_05
Patent number
US09040714B2

Reaction notes

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