Reaction #1004052

Reaction equation

sodium bicarbonate

PPTS

(2-bromo-5-fluoro-phenyl)-methanol

ethyl vinyl ether

→

title compound

Yield 83.3%

1-Bromo-2-(1-ethoxy-ethoxymethyl)4-fluoro-benzene

Yield 83.3%

Solvents

methylene chloride

Conditions

Workup

1. 1
   TemperatureWarm
2. 2
   Otherreaction to room temperature
3. 3
   workup.ADDITIONslowly after addition
4. 4
   workup.ADDITIONpour
5. 5
   Extractionextract with methylene chloride
6. 6
   DryingDry with sodium sulfate
7. 7
   Filtrationfilter
8. 8
   Concentrationconcentrate in vacuo

Procedure

Dissolve commercially available (2-bromo-5-fluoro-phenyl)-methanol (4.8 g, 23.4 mmol) in methylene chloride (100 mL) and cool to 0° C. Add PPTS (590 mg, 2.3 mmol) followed by ethyl vinyl ether (3.4 mL, 35.1 mmol). Warm reaction to room temperature slowly after addition. After 4 hours, pour the reaction into saturated aqueous sodium bicarbonate and extract with methylene chloride. Dry with sodium sulfate, filter and concentrate in vacuo to yield 5.4 g (83%) of the title compound as a clear and colorless oil. 1H NMR (CDCl3) 37.47 (dd, J=8.6, 5.0 Hz, 1M), 7.27 (dd, J=9.6, 3.1 Hz, 1H), 6.87 (td, J=8.0, 3.1 Hz, 1H), 4.89 (q, J=5.5 Hz, 1H), 4.65 (d, J=13.8 Hz, 1H), 4.54 (d, J=13.8 Hz, 1H), 3.70 (m, 1H), 3.55 (m, 1H), 1.42 (d, J=5.5 Hz, 3H), 1.22 (t, J=7.2 Hz, 3H).

Source