Sodium Hydroxide → 3-(3,6-Dibromo-9H-carbazol-9-yl)-2-hydroxypropanoic acid

HRID 1811478Notes

Reaction equation

HRID 1811478 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[N:8]([CH2:18][CH:19]([OH:24])[C:20]([O:22]C)=[O:21])[C:9]3[C:14]([C:15]=2[CH:16]=1)=[CH:13][C:12]([Br:17])=[CH:11][CH:10]=3>CCO>[Br:17][C:12]1[CH:11]=[CH:10][C:9]2[N:8]([CH2:18][CH:19]([OH:24])[C:20]([OH:22])=[O:21])[C:7]3[C:15]([C:14]=2[CH:13]=1)=[CH:16][C:4]([Br:3])=[CH:5][CH:6]=3

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58097196Methyl 3-(3,6-Dibromo-9H-carbazol-9-yl)-2-hydroxypropanoate

Product 1

HCID 580972063-(3,6-Dibromo-9H-carbazol-9-yl)-2-hydroxypropanoic acidYield 99.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

NaOH (0.64 mL, 1M solution in H2O) was added to a suspension of methyl 3-(3,6-dibromo-9H-carbazol-9-yl)-2-hydroxypropanoate (0.055 g, 0.129 mmol) in EtOH (2.6 mL) and the reaction was stirred at ambient temperature for 2.5 h. The reaction was concentrated in vacuo and the residue was acidified with 1N aqueous HCl. The mixture was extracted with EtOAc (3×), and the combined organics were washed with saturated aqueous NaCl, dried over Na2SO4, filtered, and concentrated in vacuo to afford the desired product as a white solid (53 mg, 99%).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. extractionThe mixture was extracted with EtOAc (3×)
  3. washthe combined organics were washed with saturated aqueous NaCl
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6e13aaadfe2243fdae636237cb334def
Source dataset
uspto-grants-2013_01
Patent number
US08362277B2

Reaction notes

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