Propargyl bromide → HCID 22482846, compound

HRID 2110958Notes

Reaction equation

HRID 2110958 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:13])[CH2:11][CH3:12])=[C:6]([OH:14])[CH:5]=1.Br[CH2:16][C:17]#[CH:18]>CN(C=O)C>[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:13])[CH2:11][CH3:12])=[C:6]([O:14][CH2:18][C:17]#[CH:16])[CH:5]=1

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 10678674HCID 10678674, compound

Product 1

HCID 22482846HCID 22482846, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of NaH (95%, 278 mg, 11 mmol) in DMF (20 mL) at 0° C., was added 1-(4-fluoro-2-hydroxy-phenyl)-propan-1-one (1.68 g, 10 mmol) in DMF (5 mL). After 15 min at 0° C., was 3-bromo-propyne (3.02 g, 20 mmol) added to the reaction mixture. After 1 h at 0° C., was the reaction mixture allowed to assume room temperature. The reaction mixture was extracted with H2O (100 mL). The H2O phase was washed with Et2O 3×100 mL) and the solvent of the combined organic phases was removed under reduced pressure. The crude product was purified by column chromatography (silica gel, CH2Cl2), to give 1.40 g (68%) of 1-(4-fluoro-2-prop-2-ynyloxy-phenyl)-propan-1-one.

Workup

  1. additionadded to the reaction mixture
  2. waitAfter 1 h at 0° C.
  3. customto assume room temperature
  4. extractionThe reaction mixture was extracted with H2O (100 mL)
  5. washThe H2O phase was washed with Et2O 3×100 mL) and the solvent of the combined organic phases
  6. customwas removed under reduced pressure
  7. customThe crude product was purified by column chromatography (silica gel, CH2Cl2)

Sources & evidence

ORD record
ord-45993e54743d4d99b19dc45fdfe7f39c
Source dataset
uspto-grants-2009_04
Patent number
US07517992B2

Reaction notes

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