Ethyl vinyl ether → Benzene, 1-bromo-2-[(1-ethoxyethoxy)methyl]-4-fluoro-

HRID 916870Notes

Reaction equation

HRID 916870 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH2:9][OH:10].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1.[CH:28]([O:30][CH2:31][CH3:32])=[CH2:29].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH2:9][O:10][CH:28]([O:30][CH2:31][CH3:32])[CH3:29]

Participants

6

Reactant 4

HCID 8023Ethyl vinyl etherHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium BicarbonateHCID 27733492-Bromo-5-fluorobenzyl alcohol

Product 1

HCID 58961545Benzene, 1-bromo-2-[(1-ethoxyethoxy)methyl]-4-fluoro-Yield 83.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

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).

Workup

  1. temperatureWarm
  2. customreaction to room temperature
  3. additionslowly after addition
  4. additionpour
  5. extractionextract with methylene chloride
  6. dry with materialDry with sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-f4c2ee23887444a7b4e7394fe1450ed7
Source dataset
uspto-grants-2007_09
Patent number
US07271264B2

Reaction notes

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