Boron tribromide → HCID 23594016, compound

HRID 1612061Notes

Reaction equation

HRID 1612061 reaction equation
B(Br)(Br)Br.[CH2:5]([N:12]1[C:24]2[CH:23]=[C:22]3[CH2:25][CH2:26][CH2:27][CH2:28][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[CH2:25][CH2:26][CH2:27][CH2:28][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 23594010HCID 23594010, compound

Product 1

HCID 23594016HCID 23594016, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (0.3 mL, 3.0 mM) was slowly added to a stirred solution of 5-benzyl-11-methoxy-7,8,9,10-tetrahydro-5H-benzo[b]carbazole-1-carboxylic acid, methyl ester, (0.12 g, 0.3 mM) in 5 mL methylene chloride at −10° C. After 5.5 h, the mixture was quenched with methanol (3.0 mL, 75.0 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 to afford 0.108 g (93%) of the title compound 5-benzyl-11-hydroxy-7,8,9,10-tetrahydro-5H-benzo[b]carbazole-1-carboxylic acid, methyl ester as a yellow solid (MP 174–176° C., MW 385.47).

Workup

  1. customthe mixture was quenched with methanol (3.0 mL, 75.0 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

Sources & evidence

ORD record
ord-b7fc9e083c124f1b9115726a3e9f88bd
Source dataset
uspto-grants-2006_01
Patent number
US06992100B2

Reaction notes

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