Dichloromethane → HCID 24828737, compound

HRID 2387731Notes

Reaction equation

HRID 2387731 reaction equation
C(N(CC)C(C)C)(C)C.[CH3:10][O:11][CH2:12]Cl.ClCCl.[F:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=1[OH:26])[CH:21]=[O:22]>O>[F:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=1[O:26][CH2:10][O:11][CH3:12])[CH:21]=[O:22]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 5872503-Fluoro-4-hydroxybenzaldehyde

Product 1

HCID 24828737HCID 24828737, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N,N-diisopropylethylamine (23.7 ml) and chloromethyl methyl ether (7.76 ml) were added to a dichloromethane (130 ml) solution of 3-fluoro-4-hydroxybenzaldehyde (13 g) under cooling on ice, and the obtained mixture was stirred at room temperature for 11 hours. Water was added to the reaction solution, and the mixture was extracted with dichloromethane. The obtained organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-heptane:ethyl acetate=19:1 to 7:3), so as to obtain the title compound (17.4 g).

Workup

  1. temperatureunder cooling on ice
  2. extractionthe mixture was extracted with dichloromethane
  3. dry with materialThe obtained organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (n-heptane:ethyl acetate=19:1 to 7:3)

Sources & evidence

ORD record
ord-f3ff2d302c504d03a6915b94a8fc1874
Source dataset
uspto-grants-2012_09
Patent number
US08268848B2

Reaction notes

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