Chloromethyl Methyl Ether → HCID 66701171, compound

HRID 2062116Notes

Reaction equation

HRID 2062116 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[OH:12].C(N(C(C)C)C(C)C)C.Cl[CH2:23][O:24][CH3:25].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[O:12][CH2:23][O:24][CH3:25]

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 10340Sodium CarbonateHCID 81531DiisopropylethylamineHCID 123363915-Fluoronaphthalen-1-ol

Product 1

HCID 66701171HCID 66701171, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 0.257 g of 5-fluoro-1-hydroxynaphthalene in 6 ml of dry dichloromethane was cooled in an ice/salt bath after which was added 0.36 ml (2.07 mmol) of ethyl diisopropylamine followed by 0.15 ml (0.16 g, 1.96 mmol) of chloromethylmethyl ether. The mixture was stirred at 0° C. for 0.5 h after which it was allowed to warm to RT and stirred at RT for 11 h. The mixture was poured into saturated sodium carbonate solution, extracted twice with dichloromethane, dried, filtered and concentrated to an oil. The material was dissolved in a minimum volume of dichloromethane and flash chromatographed on silica gel, eluting with ethyl acetate/heptane to provide 0.260 g (79%) of 5-fluoro-1-methoxymethyloxynaphthalene.

Workup

  1. temperatureto warm to RT
  2. stirringstirred at RT for 11 h
  3. extractionextracted twice with dichloromethane
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated to an oil
  7. dissolutionThe material was dissolved in a minimum volume of dichloromethane and flash
  8. customchromatographed on silica gel
  9. washeluting with ethyl acetate/heptane

Sources & evidence

ORD record
ord-527f369561cc472fb20ecf10fd94785e
Source dataset
uspto-grants-2012_10
Patent number
US08283479B2

Reaction notes

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