Sulfuric Acid → 2,3-Difluoro-6-trifluoromethylbenzaldehyde

HRID 1005490Notes

Reaction equation

[F:1][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([C:11]([F:14])([F:13])[F:12])[C:3]=1[C:4]#N.[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+].S(=O)(=O)(O)[OH:28]>ClCCl.C1(C)C=CC=CC=1>[F:1][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([C:11]([F:14])([F:13])[F:12])[C:3]=1[CH:4]=[O:28]

Participants

Conditions

Temperature: -78 °C

Procedure

2.0 g of 2,3-difluoro-6-trifluoromethylbenzonitrile was dissolved in 20 ml of anhydrous dichloromethane and the resultant solution was cooled down to -78° C. under a nitrogen atmosphere. To the solution was then gradually added dropwise with 7.1 ml of 1.5 M toluene solution of diisobutyl aluminium hydride (DIBAL) over 30 minutes. After stirring the solution at -78° C. for 1 hour, the solution was allowed to room temperature. The solution was then added with 7 ml of saturated aqueous solution of ammonium chloride, stirred for 30 minutes and subsequently added with 33 ml of 5% sulfuric acid. The mixture was then extracted with ether, and the organic layer obtained was washed with saturated saline solution and was then dried over anhydrous magnesium sulfate. After a process for the concentration, the organic solution was purified by using silica gel column chromatography to obtain 1.36 g of the title compound (nD 20.6-1.4357).

Workup

customwas allowed to room temperature
stirringstirred for 30 minutes
extractionThe mixture was then extracted with ether
customthe organic layer obtained
washwas washed with saturated saline solution
dry with materialwas then dried over anhydrous magnesium sulfate
concentrationAfter a process for the concentration
customthe organic solution was purified

Sources & evidence

ORD record: ord-7ae59446d3a04adf955b8cff466a5489
Source dataset: uspto-grants-2000_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06054605

Reaction notes

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