Ammonium Chloride → HCID 23525916, compound

HRID 2415442Notes

Reaction equation

HRID 2415442 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1[CH:10]=[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH:8]=[CH:7][C:6]=1[I:20].[H-].C([Al+2])C(C)C.[H-].[NH4+].[Cl-]>ClCCl>[F:19][C:16]1[CH:15]=[CH:14][C:13]([CH2:12][O:11][C:9]2[CH:8]=[CH:7][C:6]([I:20])=[C:5]([CH2:4][CH:3]=[O:2])[CH:10]=2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21862895HCID 21862895, compoundHCID 23525933HCID 23525933, compound

Product 1

HCID 23525916HCID 23525916, compoundYield 103.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

[5-(4-Fluoro-benzyloxy)-2-iodo-phenyl)-acetic acid methyl ester (12.6 g, 31.4 mmol), was dissolved under argon in 126 mL of dichloromethane and then, at −78° C., isobutylaluminum hydride (29.1 mL, 34.8 mmol) was added dropwise. The reaction mixture was stirred at −78° C. for 6 h until the TLC indicated the end of the reaction. A saturated solution of NH4Cl was added and the reaction mixture was allowed to come to room temperature. Dichloromethane was added, the organic phase was separated and the aqueous layer extracted with dichloromethane. Drying over magnesium sulfate and concentration in a rotatory evaporator gave the aldehyde (12 g, 100%) that was used in the next step without purification.

Workup

  1. customthe end of the reaction
  2. customto come to room temperature
  3. customthe organic phase was separated
  4. extractionthe aqueous layer extracted with dichloromethane
  5. dry with materialDrying over magnesium sulfate and concentration in a rotatory evaporator

Sources & evidence

ORD record
ord-ecadb6aaea264ba9ae4305b272489e17
Source dataset
uspto-grants-2004_11
Patent number
US06818774B2

Reaction notes

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