Sodium Carbonate → 2'-Hydroxy-3'-phenyl-5'methylacetophenone

HRID 983803Notes

Reaction equation

HRID 983803 reaction equation
[OH:1][C:2]1[C:7](Br)=[CH:6][C:5]([CH3:9])=[CH:4][C:3]=1[C:10](=[O:12])[CH3:11].[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O>[OH:1][C:2]1[C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:6][C:5]([CH3:9])=[CH:4][C:3]=1[C:10](=[O:12])[CH3:11]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 111389181-(3-Bromo-2-hydroxy-5-methylphenyl)ethan-1-one

Product 1

HCID 111280072'-Hydroxy-3'-phenyl-5'methylacetophenoneYield 71.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
75 °C

Procedure

2′-Hydroxy-3′-bromo-5′methylacetophenone 233 (0.46 g, 2 mmol) and phenylboronic acid (0.24 g, 1 eq.) are dissolved in DME (10 ml) and placed under a nitrogen atmosphere. Na2CO3 (0.50 g, 3 eq.) in water (10 ml) is added, followed by Pd(Ph3)4 (0.12 g, 0.05 eq.) and the reaction mixture heated to 75° C. for 12-18 h. Most of the DME is removed in vacuo and the reaction mixture is diluted with ether, washed with water, brine, and dried (MgSO4), and concentrated in vacuo to give an oil. Purification by flash chromatography (5/95 EtOAc/hexanes) afforded 2′-Hydroxy-3′-phenyl-5′methylacetophenone 234 as a yellow solid (0.32 g, 71% yield) (Example 519, Table IIIa).

Workup

  1. customMost of the DME is removed in vacuo
  2. additionthe reaction mixture is diluted with ether
  3. washwashed with water, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give an oil
  7. customPurification by flash chromatography (5/95 EtOAc/hexanes)

Sources & evidence

ORD record
ord-48bf3c8f885a4f01b822992c534ab589
Source dataset
uspto-grants-2005_03
Patent number
US06867200B1

Reaction notes

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