Boron tribromide → HCID 23594017, compound

HRID 1612052Notes

Reaction equation

HRID 1612052 reaction equation
B(Br)(Br)Br.[CH2:5]([N:12]1[C:24]2[CH:23]=[C:22]3[CH:25]=[CH:26][CH:27]=[CH:28][C:21]3=[C:20]([O:29]C)[C:19]=2[C:18]2[C:17]([C:31]([O:33][CH3:34])=[O:32])=[CH:16][CH:15]=[CH:14][C:13]1=2)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(Cl)Cl>[CH2:5]([N:12]1[C:24]2[CH:23]=[C:22]3[CH:25]=[CH:26][CH:27]=[CH:28][C:21]3=[C:20]([OH:29])[C:19]=2[C:18]2[C:17]([C:31]([O:33][CH3:34])=[O:32])=[CH:16][CH:15]=[CH:14][C:13]1=2)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 23594014HCID 23594014, compound

Product 1

HCID 23594017HCID 23594017, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (0.148 mL, 1.56 mM) was slowly added to a stirred solution of 5-benzyl-11-methoxy-5H-benzo[b]carbazole-1-carboxylic acid, methyl ester, (0.474 g, 1.2 mM) in 8 mL methylene chloride at −10° C. After 1.5 h, the mixture was quenched with methanol (1.22 mL, 30.0 mM) and allowed to warm to room temperature with stirring over 2 h. The mixture was diluted with methylene chloride, washed with H2O, 1N HCl, saturated aqueous NaHCO3 solution, and saturated brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resultant orange-brown solid was purified by column chromatography on silica gel (elution with gradient hexane/ethyl acetate) to afford 0.245 g (47%) of the title compound 5-benzyl-11-hydroxy-5H-benzo[b]carbazole-1-carboxylic acid, methyl ester as an orange foam (MW 381.44).

Workup

  1. customthe mixture was quenched with methanol (1.22 mL, 30.0 mM)
  2. additionThe mixture was diluted with methylene chloride
  3. washwashed with H2O, 1N HCl, saturated aqueous NaHCO3 solution, and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resultant orange-brown solid was purified by column chromatography on silica gel (elution with gradient hexane/ethyl acetate)

Sources & evidence

ORD record
ord-68a8b0d9bc5f4a5cb6ec0b73a6ac2b6f
Source dataset
uspto-grants-2006_01
Patent number
US06992100B2

Reaction notes

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