Sodium Hydroxide → 6-Bromo-7-fluoro-2-phenylchroman-4-one

HRID 1408786Notes

Reaction equation

HRID 1408786 reaction equation
[Br:1][C:2]1[C:3]([F:19])=[CH:4][C:5]([OH:18])=[C:6]([C:8](=[O:17])[CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=1.[OH-].[Na+]>O.CCO>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][C:3]=1[F:19])[O:18][CH:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:9][C:8]2=[O:17]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 671755841-(5-Bromo-4-fluoro-2-hydroxyphenyl)-3-phenylprop-2-en-1-one

Product 1

HCID 584240016-Bromo-7-fluoro-2-phenylchroman-4-oneYield 54%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1-(5-Bromo-4-fluoro-2-hydroxyphenyl)-3-phenylprop-2-en-1-one (10.8 g, 33.75 mmol) was dissolved in H2O (252 mL) and EtOH (84 mL). Then NaOH (1.35 g, 33.75 mmol) was added. The mixture was stirred overnight and filtered. The cake was dissolved in EtOAc and washed with H2O twice. The organic layer was dried and filtered. The filtrate was concentrated to give 6-bromo-7-fluoro-2-phenylchroman-4-one (5.8 g, 54%). 1H-NMR (CDCl3): 2.85 (m, 1H), 3.04 (m, 1H), 5.43 (m, 1H), 6.78 (m, 1H), 7.37 (m, 5H), 8.07 (m, 1H).

Workup

  1. filtrationfiltered
  2. dissolutionThe cake was dissolved in EtOAc
  3. washwashed with H2O twice
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-e2d63f1bb9144a9f9380918246d0fb73
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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