Water → HCID 59426447, compound

HRID 907104Notes

Reaction equation

HRID 907104 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 was 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 was added dropwise at 0° C. After the addition, the mixture was stirred at 0° C. for 2 h. After the addition of H2O, the organic phase was separated and washed with brine and dried over Na2SO4. The solvent was then concentrated and the residue was 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 was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationThe solvent was then concentrated
  6. customthe residue was purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-42699ca4d3e94b3db18a5ef6fe1b59f1
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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