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

HRID 2096599Notes

Reaction equation

HRID 2096599 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-6be9a9e54f4a4b599079cda132ab597e
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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