Sodium Hydroxide → HCID 58424325, compound

HRID 1408598Notes

Reaction equation

HRID 1408598 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:19])=[C:6]([C:8](=[O:18])[CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=2)[CH:7]=1.[OH-].[Na+]>O.CCO>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:19][CH:10]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=1)[CH2:9][C:8]2=[O:18]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67174273HCID 67174273, compound

Product 1

HCID 58424325HCID 58424325, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1-(5-Bromo-2-hydroxyphenyl)-3-(3-chlorophenyl)prop-2-en-1-one (23 g, 68 mmol) was dissolved in H2O (513 mL) and EtOH (171 mL). Then NaOH (2.74 g, 68 mmol) was added. The mixture was stirred overnight and filtered. The solid was dissolved in EtOAc and washed with H2O twice. The organic layer was dried and filtered. The filtrate was concentrated to give 6-bromo-2-(3-chlorophenyl)chroman-4-one (18.82 g, 82%). 1H-NMR (CDCl3): 2.87 (m, 1H), 3.02 (m, 1H), 5.44 (m, 1H), 6.96 (d, 1H), 7.31 (m, 1H), 7.37 (m, 2H), 7.48 (s, 1H), 7.58 (m, 1H), 8.02 (d, 1H).

Workup

  1. filtrationfiltered
  2. dissolutionThe solid 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-c60207a7a7004b30af8f869b8acbd55f
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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