Water → HCID 59426447, compound

HRID 506003Notes

Reaction equation

HRID 506003 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-fd762ac465ee4dec83732a6cab26d2f0
Source dataset
uspto-grants-2010_08
Patent number
US07781478B2

Reaction notes

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