Chloromethyl Methyl Ether → HCID 88909600, compound

HRID 926922Notes

Reaction equation

HRID 926922 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:10]=1[I:16])([OH:8])[C:4]([F:7])([F:6])[F:5].[CH3:19][O:20][CH2:21]Cl>C(N(CC)C(C)C)(C)C>[F:18][C:2]([F:1])([F:17])[C:3]([C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:10]=1[I:16])([O:8][CH2:19][O:20][CH3:21])[C:4]([F:7])([F:6])[F:5]

Participants

4

Reactant 2

HCID 7864Chloromethyl Methyl EtherHCID 3295551,1,1,3,3,3-hexafluoro-2-(2-iodo-5-methylphenyl)propan-2-ol

Product 1

HCID 88909600HCID 88909600, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 81531DiisopropylethylamineSolvent

Procedure

Compound 2 (4 g, 10.42 mmol) was dissolved in N,N-diisopropylethylamine (DIPEA, 20 mL) freshly distilled over calcium hydride. The solution was cooled in an ice-bath and the chloromethyl methyl ether (4.75 mL, 62.5 mmol) was added. A white precipitate appeared instantaneously. The reaction mixture was stirred overnight at room temperature. After removal of DIPEA under vacuum, the residue was chromatographied over silica gel using heptane/acetone (97/3) to give 4.23 g (9.89 mmol, 95% yield) of a slightly yellow solid.

Workup

  1. distillationfreshly distilled over calcium hydride
  2. temperatureThe solution was cooled in an ice-bath
  3. customAfter removal of DIPEA under vacuum
  4. customto give 4.23 g (9.89 mmol, 95% yield) of a slightly yellow solid

Sources & evidence

ORD record
ord-fcee7cd1fe294904807e4f16b9a5f730
Source dataset
uspto-grants-2016_03
Patent number
US09290421B2

Reaction notes

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