2-Chloromethyl 2-(trimethylsilyl)ethyl ether → HCID 19707461, compound

HRID 726751Notes

Reaction equation

HRID 726751 reaction equation
[CH3:1][Si:2]([CH3:9])([CH3:8])[CH2:3][CH2:4][O:5][CH2:6]Cl.[Br:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([OH:26])([C:22]([F:25])([F:24])[F:23])[C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=1>C(Cl)Cl.C(Cl)(Cl)Cl>[Br:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]([O:26][CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:9])([CH3:8])[CH3:1])([C:18]([F:19])([F:20])[F:21])[C:22]([F:24])([F:25])[F:23])=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 232335702-(4-Bromophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol

Product 1

HCID 19707461HCID 19707461, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(trimethylsilyl)ethoxymethyl chloride (25.9 g, 0.155 mol) in CH2Cl2 (50 mL) was added dropwise to a solution of 2-(4-bromophenyl)-1,1,1,3,3,3-hexafluoro-2-propanol from Step 1 (38.6 g, 0.120 mol) in the same solvent (500 mL) at 0° C. After completion of the addition, the mixture was allowed to warm to room temperature, and stirred for 3 h before it was diluted with CHCl3 (500 mL). The resulting solution was washed successively with 1N HCl (2×), saturated aqueous NaHCO3, water and brine, dried (Na2SO4) and concentrated. The residue was distilled under reduced pressure (bp 128° C./0.9 mmHg) to afford the title compound as a colorless liquid (50.0 g, 92%).

Workup

  1. additionAfter completion of the addition
  2. washThe resulting solution was washed successively with 1N HCl (2×), saturated aqueous NaHCO3, water and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. distillationThe residue was distilled under reduced pressure (bp 128° C./0.9 mmHg)

Sources & evidence

ORD record
ord-b46161dfd4eb4f65a3d949da146adc83
Source dataset
uspto-grants-1998_01
Patent number
US05710170

Reaction notes

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