Triethylamine → 4-(5-Bromo-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal

HRID 1869347Notes

Reaction equation

HRID 1869347 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH3:21])=[C:6]([C:8]([CH3:19])([CH3:18])[CH2:9][C:10]([OH:17])([C:13]([F:16])([F:15])[F:14])[CH2:11][OH:12])[CH:7]=1.C(N(CC)CC)C.[Cl-].[NH4+].C(OC)(C)(C)C>ClCCl.CS(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH3:21])=[C:6]([C:8]([CH3:19])([CH3:18])[CH2:9][C:10]([OH:17])([C:13]([F:16])([F:15])[F:14])[CH:11]=[O:12])[CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 15413tert-Butyl methyl etherHCID 25517Ammonium ChlorideHCID 179891794-(5-Bromo-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentan-1-ol

Product 1

HCID 179891754-(5-Bromo-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanalYield 79.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

1.13 g (3.06 mmol) of 4-(5-bromo-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentan-1-ol is added in 20 ml of dichloromethane and 5.4 ml of DMSO. After mixing with 1.55 g (15.32 mmol) of triethylamine and 975.28 mg (6.13 mmol) of SO3/pyridine complex, the batch is stirred overnight at room temperature. After TLC, another spatula tip full of SO3/pyridine complex is added, and it is further stirred for several hours. The reaction mixture is mixed with saturated ammonium chloride solution and shaken out three times with methyl tert-butyl ether. The combined organic extracts are washed with water and brine. After the solvent is dried and spun off, the residue is chromatographed on a Flashmaster. 902.7 mg (79.81%) of the desired aldehyde (together with the Desbrom compound) is isolated.

Workup

  1. additionAfter TLC, another spatula tip full of SO3/pyridine complex is added
  2. stirringit is further stirred for several hours
  3. washThe combined organic extracts are washed with water and brine
  4. customAfter the solvent is dried
  5. customthe residue is chromatographed on a Flashmaster

Sources & evidence

ORD record
ord-60961f820fbb49ffbf4a082b3ff1957d
Source dataset
uspto-grants-2009_12
Patent number
US07638515B2

Reaction notes

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