Chloromethyl Methyl Ether → 2-Fluoro-6-hydroxy-4-(methoxymethoxy)benzaldehyde

HRID 217429Notes

Reaction equation

HRID 217429 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([OH:11])[C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:19][O:20][CH3:21]>CC#N>[F:1][C:2]1[CH:9]=[C:8]([O:10][CH2:19][O:20][CH3:21])[CH:7]=[C:6]([OH:11])[C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 10796Cesium carbonateHCID 220104032-Fluoro-4,6-dihydroxybenzaldehyde

Product 1

HCID 584391082-Fluoro-6-hydroxy-4-(methoxymethoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Fluoro-4,6-dihydroxybenzaldehyde (12 g) was dissolved in MeCN (250 mL), and cesium carbonate (25.1 g) and chloromethylmethylether (6.95 mL) were added thereto, followed by stirring at room temperature for 1 hour. The insoluble materials were removed by filtration through celite and the filtrate was concentrated. The residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=100:0 to 94:6) to obtain 2-fluoro-6-hydroxy-4-(methoxymethoxy)benzaldehyde (11.89 g) as a white powder.

Workup

  1. customThe insoluble materials were removed by filtration through celite
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=100:0 to 94:6)

Sources & evidence

ORD record
ord-bacb46623168401e913635ea2b20f795
Source dataset
uspto-grants-2012_06
Patent number
US08193378B2

Reaction notes

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