Potassium Carbonate → 2,4-Dichloro-6-(4-fluorophenylmethoxy)benzaldehyde

HRID 1199915Notes

Reaction equation

HRID 1199915 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[C:5]([CH:6]=[O:7])=[C:4]([OH:11])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[F:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[CH:21][CH:20]=1>CN(C=O)C>[Cl:10][C:8]1[CH:9]=[C:2]([Cl:1])[CH:3]=[C:4]([O:11][CH2:23][C:22]2[CH:25]=[CH:26][C:19]([F:18])=[CH:20][CH:21]=2)[C:5]=1[CH:6]=[O:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 5283902,4-Dichloro-6-hydroxybenzaldehyde

Product 1

HCID 135532412,4-Dichloro-6-(4-fluorophenylmethoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 13.77 g (72.5 mmol) of 4,6-dichloro-2-hydroxybenzaldehyde in 100 ml of DMF was stirred and 12.02 g (87 mmol) of K2CO3 was added. This mixture was heated to ~70° C. for 60 minutes, then 11.7 ml of 4-fluorobenzyl bromide was added. The resulting solution was stirred at 70° C. for 3.5 hours, then this was poured onto ice H2O (1.5 l), filtered and washed with H2O, and recrystallized from Et2O/petroleum ether. Yield: 17.88 g (83%) of off-white crystals, m.p. 107°-108° C.

Workup

  1. temperatureThis mixture was heated to ~70° C. for 60 minutes
  2. additionthis was poured onto ice H2O (1.5 l)
  3. filtrationfiltered
  4. washwashed with H2O
  5. customrecrystallized from Et2O/petroleum ether

Sources & evidence

ORD record
ord-dadefa8e8a9d4ae7b0db43de5f59819d
Source dataset
uspto-grants-1990_02
Patent number
US04904646

Reaction notes

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