Chloromethyl Methyl Ether → 1-(Methoxymethoxy)-2-(trifluoromethoxy)benzene

HRID 1911277Notes

Reaction equation

HRID 1911277 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10].C(N(CC)C(C)C)(C)C.[CH3:22][O:23][CH2:24]Cl>ClCCl.CC(OC)(C)C>[CH3:22][O:23][CH2:24][O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[O:3][C:2]([F:11])([F:12])[F:1]

Participants

6

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 27772992-(Trifluoromethoxy)phenol

Product 1

HCID 121796491-(Methoxymethoxy)-2-(trifluoromethoxy)benzeneYield 93%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

A solution of 2-(trifluoromethyloxy)phenol (12.0 g, 67.4 mmol) in dichloromethane (45 mL) was cooled to 5° C., and N,N-diisopropylethylamine (23.5 mL, 135 mmol) and methoxymethyl chloride (7.68 mL, 135 mmol) were added dropwise, keeping the internal temperature≦15° C. The reaction mixture was warmed to ambient temperature, stirred for 15 min at ambient temperature, then diluted with MTBE (250 mL) and washed with 2N HCl (2×50 mL), water (50 mL), 2N NaOH (2×30 mL), water (30 mL), and brine (30 mL). The organic portion was dried (Na2SO4), filtered, and concentrated to give the title compound (13.9 g, 62.6 mmol, 93%). which was used without further purification. MS (DCI/NH3) m/z 222 (M+H)+.

Workup

  1. customthe internal temperature≦15° C
  2. washwashed with 2N HCl (2×50 mL), water (50 mL), 2N NaOH (2×30 mL), water (30 mL), and brine (30 mL)
  3. dry with materialThe organic portion was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-00e4ff84dd5348bbb4b04dcc63ce2ec1
Source dataset
uspto-grants-2013_12
Patent number
US08604053B2

Reaction notes

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