1-Fluoronaphthalene → 4-Fluoronaphthalene-1-carbaldehyde

HRID 388363Notes

Reaction equation

HRID 388363 reaction equation
Cl[Sn](Cl)(Cl)Cl.ClC([O:9][CH3:10])Cl.[F:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1>ClCCl>[F:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH:10]=[O:9])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 94501-FluoronaphthaleneHCID 21004Methane, dichloromethoxy-HCID 24287Tin tetrachloride

Product 1

HCID 70225244-Fluoronaphthalene-1-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

SnCl4 (13 ml, 1M solution in dichloromethane) is added to a solution of dichlormethyl-methylether in dichloromethane (6 ml) at 0° C. After 1 hour at 0° C., a solution of 1-fluoro-naphtalene (1.46 g) in dichloromethane (4 ml) is added over 10 minutes. The reaction is stirred overnight at room temperature and then quenched with cold water (30 ml). The organic phase is separated and the aqueous phase is extracted 3 times with dichloromethane. The combined organic phases are dried over Na2SO4 and concentrated in vacuo to yield 4-fluoro-naphthalene-1-carbaldehyde (1.73 g, dark brown crystals). The crude product obtained is used without further purification, MS (HPLC/MS): no ionisation. Retention time: 3.88 min.

Workup

  1. customquenched with cold water (30 ml)
  2. customThe organic phase is separated
  3. extractionthe aqueous phase is extracted 3 times with dichloromethane
  4. dry with materialThe combined organic phases are dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f78f64f5e1bc4f0daf14473a3feb52c6
Source dataset
uspto-grants-2013_02
Patent number
US08377942B2

Reaction notes

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