Sodium hydride → 7-Fluoro-3,4-dihydro-1-benzoxepin-5(2H)-one

HRID 1190720Notes

Reaction equation

HRID 1190720 reaction equation
[H-].[Na+].Br[CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:8]=1[C:14](=[O:16])[CH3:15]>C1COCC1>[F:13][C:10]1[CH:11]=[CH:12][C:7]2[O:6][CH2:5][CH2:4][CH2:15][C:14](=[O:16])[C:8]=2[CH:9]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 58203950HCID 58203950, compound

Product 1

HCID 122435647-Fluoro-3,4-dihydro-1-benzoxepin-5(2H)-oneYield 56.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Weighed out Sodium Hydride (561 mg, 23.4 mmol) into a nitrogen purged round bottom flask and added 10 mL THF. Placed the solution under nitrogen and added 1-(2-(2-bromoethoxy)-5-fluorophenyl)ethanone (4.07 g, 15.6 mmol) in 15 mL THF. Let stir at room temperature overnight. Concentrated in vacuo and flashed 0 to 50% ethyl acetate/hexanes. NMR confirmed product as 7-fluoro-3,4-dihydrobenzo[b]oxepin-5(2H)-one (1.58 g, 56.2% yield).

Workup

  1. concentrationConcentrated in vacuo

Sources & evidence

ORD record
ord-5bd31424cd434eda8537d319b1cb8dc7
Source dataset
uspto-grants-2014_03
Patent number
US08673952B2

Reaction notes

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