Lithium Carbonate → 3'-Hydroxy-4'-(2,6-difluorobenzyloxy)-acetophenone

HRID 1596703Notes

Reaction equation

HRID 1596703 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[OH:8].C(=O)([O-])[O-].[Li+].[Li+].Br[CH2:19][C:20]1[C:25]([F:26])=[CH:24][CH:23]=[CH:22][C:21]=1[F:27]>CN(C)C=O>[OH:1][C:2]1[CH:3]=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[O:8][CH2:19][C:20]1[C:25]([F:26])=[CH:24][CH:23]=[CH:22][C:21]=1[F:27]

Participants

5

Reactant 3

HCID 11125Lithium CarbonateHCID 145303',4'-DihydroxyacetophenoneHCID 5814352-(Bromomethyl)-1,3-difluorobenzene

Product 1

HCID 105167073'-Hydroxy-4'-(2,6-difluorobenzyloxy)-acetophenone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3′,4′-dihydroxyacetophenone (25.0 g, 164.3 mmol), lithium carbonate (12.1 g, 164.3 mmol), and α-bromo-2,6-difluorotoluene (34.0 g, 164.3 mmol) in dimethyl formamide (400 mL) is stirred at room temperature for 2 days. The mixture is then filtered through celite, and the filtrate is concentrated in vacuo. The residue is diluted with H2O(200 mL), and the mixture is filtered. The collected solid is recrystallized from ethanol to give 3′-hydroxy-4′-(2,6-difluorobenzyloxy)-acetophenone.

Workup

  1. filtrationThe mixture is then filtered through celite
  2. concentrationthe filtrate is concentrated in vacuo
  3. additionThe residue is diluted with H2O(200 mL)
  4. filtrationthe mixture is filtered
  5. customThe collected solid is recrystallized from ethanol

Sources & evidence

ORD record
ord-4f90ac559ab447b1b1a32448c16bb731
Source dataset
uspto-grants-2001_09
Patent number
US06291530B1

Reaction notes

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