Hydrochloric Acid → 1-Chloro-3-fluoro-2-[(1,1-dimethylethoxy)-methyl]benzene

HRID 1739654Notes

Reaction equation

HRID 1739654 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH2:4]Cl.[CH3:11][C:12]([CH3:15])([O-:14])[CH3:13].[Na+].C1(C)C=CC=CC=1.Cl>C1OCCOCCOCCOCCOC1.O>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH2:4][O:14][C:12]([CH3:15])([CH3:13])[CH3:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 1086751-Chloro-2-(chloromethyl)-3-fluorobenzeneHCID 23676156Sodium t-butoxide

Product 1

HCID 218362781-Chloro-3-fluoro-2-[(1,1-dimethylethoxy)-methyl]benzeneYield 89.9%

Reagents, catalysts & solvents 2

HCID 3633615-Crown-5CatalystHCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 200 g (1.117 mole) of 2-chloro-6 fluorobenzyl chloride, 118 g (1.23 mole) of sodium t-butoxide, 2.2 mL (11 mmole) of 15-crown-5 (15-C-5) and 1.2 L of toluene was heated at reflux temperature for four hours. After allowing the reaction mixture to cool to 45° C., 600 mL of water was added followed by 90 mL of 2N HCl. After separation, the organic phase was concentrated in vacuo to give a dark oil. Distillation using a 5-tray Oldershaw column, sand bath to 155° C., gave 217.5 g of 1-chloro-3-fluoro-2-[(1,1-dimethylethoxy)methyl]-benzene as a clear liquid (bp 60-64° C./0.6 mm Hg.).

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for four hours
  3. customAfter separation
  4. concentrationthe organic phase was concentrated in vacuo
  5. customto give a dark oil
  6. distillationDistillation
  7. customto 155° C.

Sources & evidence

ORD record
ord-23fdde5ee5154e2698d8df8c1480f4fb
Source dataset
uspto-grants-1999_10
Patent number
US05968875

Reaction notes

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