2,2,2-Cryptand → 4-(Fluoromethyl)benzaldehyde

HRID 217556

Reaction equation

HRID 217556 reaction equation
[F-:1].[K+].C1N2CCOCCOCCN(CCOCCOCC2)CCOCCOC1.CS([O:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([CH:41]=O)=[CH:37][CH:36]=1)(=O)=O>C(#N)C>[F:1][CH2:41][C:38]1[CH:39]=[CH:40][C:35]([CH:34]=[O:33])=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 728012,2,2-CryptandHCID 522689Potassium FluorideHCID 12134352HCID 12134352, compound

Product 1

HCID 214079014-(Fluoromethyl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

KF (2.7 mg, 0.047 mmol) and kryptofix 222 (17.6 mg, 0.047 mmol) were dissolved in acetonitrile (1 ml) and added to (4-formylphenyl)methyl methanesulfonate (10 mg, 0.047 mmol) in acetonitrile (1 ml). The reaction mixture was heated to 65 degrees for 10 minutes. The crude product was purified using a silica short column and diethyl ether. (Analytical HPLC: column Phenomenex Luna 00B-4251-E0, solvents: A=water/0.1% TFA and B=CH3CN/0.1% TFA; gradient 5-50% B over 10 min; flow 2.0 ml/minute; retention time 5.1 minutes detected at 214 and 254 nm).

Workup

  1. temperatureThe reaction mixture was heated to 65 degrees for 10 minutes
  2. customThe crude product was purified

Sources & evidence

ORD record
ord-1030369a0e3c4e0385f32c9e98a65080
Source dataset
uspto-grants-2012_06
Patent number
US08197793B2

Linked notes

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