Chlorotrimethylsilane → 2,4-Difluoro-1-[(trimethylsilyl)oxy]benzene

HRID 1464829Notes

Reaction equation

HRID 1464829 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].C(N(CC)CC)C.[CH3:17][Si:18]([CH3:21])([CH3:20])Cl>ClCCl>[CH3:17][Si:18]([CH3:21])([CH3:20])[O:9][C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 1230512,4-Difluorophenol

Product 1

HCID 190865902,4-Difluoro-1-[(trimethylsilyl)oxy]benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In a 2.5 l sulfation flask, 260.2 g (2.0 mol) of 2,4-difluorophenol and 242.9 g (2.4 mol) of triethylamine are dissolved in 700 ml of dichloromethane and cooled to 0° C. 239 g (2.2 mol) of trimethylchlorosilane are added dropwise in the course of about 3 hours. The white suspension is allowed to react to completion for 8 hours (check using GC and TLC). The suspension is filtered, the residue is washed with a little dichloromethane, and the filtrate is evaporated on a rotary evaporator. The oil obtained is distilled at 56°-62° C. in vacuo (22 mbar). 280 g of a clear, colourless liquid are obtained.

Workup

  1. customto react to completion for 8 hours (check using GC and TLC)
  2. filtrationThe suspension is filtered
  3. washthe residue is washed with a little dichloromethane
  4. customthe filtrate is evaporated on a rotary evaporator
  5. customThe oil obtained
  6. distillationis distilled at 56°-62° C. in vacuo (22 mbar)
  7. custom280 g of a clear, colourless liquid are obtained

Sources & evidence

ORD record
ord-50fa81c0cc8a471697c2bf4e9bd67fd3
Source dataset
uspto-grants-1994_04
Patent number
US05306600

Reaction notes

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