Allyl bromide → Methyl 2,3-dihydro-6-fluoro-4-(2-propenyl)-4H-1-benzopyran-4-carboxylate

HRID 487209Notes

Reaction equation

HRID 487209 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:12]([O:14][CH3:15])=[O:13].[H-].[Na+].[CH2:18](Br)[CH:19]=[CH2:20].[Cl-].[NH4+]>CN(C)C=O>[F:1][C:2]1[CH:11]=[CH:10][C:9]2[O:8][CH2:7][CH2:6][C:5]([CH2:20][CH:19]=[CH2:18])([C:12]([O:14][CH3:15])=[O:13])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 14986536Methyl 6-fluorochromane-4-carboxylate

Product 1

HCID 19094435Methyl 2,3-dihydro-6-fluoro-4-(2-propenyl)-4H-1-benzopyran-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of methyl 6-fluorochromane-4-carboxylate (2.1 g) in anhydrous N,N-dimethylformamide was added to a suspension of sodium hydride (265 mg) in anhydrous N,N-dimethylformamide under nitrogen. After gas evolution ceased, the mixture was cooled to 0° C., and neat allyl bromide (0.95 mL) was added. After 1 hour, 20 mL of an aqueous saturated ammonium chloride solution was added, and the mixture extracted with ethyl acetate, the extracts washed with water, brine, dried over anhydrous sodium sulfate, filtered and evaporated to afford the title compound as a colorless oil, 2.4 g. (HRMS calc'd 250.1004; found 250.1002).

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. washthe extracts washed with water, brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-207f89b7fa854ea698902b91f0fa7f70
Source dataset
uspto-grants-1994_03
Patent number
US05294635

Reaction notes

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