1-Fluoronaphthalene → 4-Fluoronaphthalene-1-carbaldehyde

HRID 1362029Notes

Reaction equation

HRID 1362029 reaction equation
C[O:2][CH:3](Cl)Cl.Cl[Sn](Cl)(Cl)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>C(Cl)Cl>[F:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH:3]=[O:2])=[CH:14][CH:13]=1

Participants

5

Reactant 3

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

Product 1

HCID 70225244-Fluoronaphthalene-1-carbaldehydeYield 87.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of α,α-dichloromethyl methyl ether (5.9 mL, 65 mmol) in CH2Cl2 (30 mL) was cooled in an ice bath and then treated dropwise over 15 min with SnCl4 (7.6 mL, 65 mmol). After stirring for 45 min, a solution of 1-fluoronaphthalene (5.5 mL, 50 mmol) in CH2Cl2 (30 mL) was added. The mixture was allowed to slowly warm to room temperature while stirring overnight. The mixture was poured in ice water (100 mL) and diluted with CH2Cl2 (50 mL). The layers were separated. The organic layer was diluted with CH2Cl2 (100 mL), washed with H2O (3×50 mL), dried over Na2SO4, filtered, and the solvent was removed in vacuo to give the title compound (7.62 g, 87%) as a pale yellow solid: MS (ESI) m/e 175 (M+H)+.

Workup

  1. stirringwhile stirring overnight
  2. customThe layers were separated
  3. additionThe organic layer was diluted with CH2Cl2 (100 mL)
  4. washwashed with H2O (3×50 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-0c8be1f301b94ac38d696eab24853792
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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