Water → HCID 59426447, compound

HRID 502122Notes

Reaction equation

HRID 502122 reaction equation
[CH:1](Cl)([F:3])[F:2].[OH:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[C:10]([CH3:23])=[C:9]2[C:24]([O:26][CH2:27][CH3:28])=[O:25].[OH-].[Na+].O>C(Cl)Cl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:2][CH:1]([F:3])[O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([C:15]1[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1)[C:10]([CH3:23])=[C:9]2[C:24]([O:26][CH2:27][CH3:28])=[O:25]

Participants

7

Reactant 4

HCID 962WaterHCID 6372ChlorodifluoromethaneHCID 14798Sodium HydroxideHCID 735531HCID 735531, compound

Product 1

HCID 59426447HCID 59426447, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Freon-22 (HCF2Cl) gas is bubbled into a solution of ethyl 5-hydroxy-1-(4-methoxyphenyl)-2-methyl-1H-indole-3-carboxylate (250 mg, 0.77 mmol) in CH2Cl2 (5 mL) at 0° C. containing a small amount of tetrabutylammonium bromide as a phase transfer catalyst. A 50% solution of NaOH is added dropwise at 0° C. After the addition, the mixture is stirred at 0° C. for 2 h. After the addition of H2O, the organic phase is separated and washed with brine and dried over Na2SO4. The solvent is then concentrated and the residue is purified by column chromatography over silica gel using EtOAc/petroleum ether (1/2) as eluent to yield the desired product in 40% yield.

Workup

  1. additionAfter the addition
  2. customthe organic phase is separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationThe solvent is then concentrated
  6. customthe residue is purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-a8920079e1dd4b99a310d1ba8860a061
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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