Ethylene Glycol → 2-(4-Bromo-2-Fluorophenyl)-1,3-Dioxolane

HRID 1172882Notes

Reaction equation

HRID 1172882 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([F:10])[CH:3]=1.[CH2:11](O)[CH2:12][OH:13].C(OCC)(OCC)OCC.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCCl>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]2[O:13][CH2:12][CH2:11][O:7]2)=[C:4]([F:10])[CH:3]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 31214Ethyl orthoformateHCID 1435174-Bromo-2-fluorobenzaldehyde

Product 1

HCID 219386012-(4-Bromo-2-Fluorophenyl)-1,3-Dioxolane

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

4-bromo-2-fluorobenzaldehyde (9.4 g, 46.3 mmol), ethylene glycol (13.2 mL), triethyl orthoformate (6.6 mL) and p-toluenesulfonic acid (0.09 g, 0.473 mmol) were stirred in DCE (50 mL) at 80° C. for 2.5 hours. Room temperature was attained and the solution was washed successively with saturated NaHCO3, H2O and brine, dried over MgSO4 and concentrated in vacuo to give the product (pale yellow oil). 1H NMR (CDCl3) δ 7.41 (t, J=8.1 Hz, 1H), 7.30 (dd, J=8.1, 1.8 Hz, 1H), 7.25 (dd, J=9.6, 1.8 Hz, 1H), 6.02 (s, 1H), 4.13 (m, 2H), 4.04 (m, 2H).

Workup

  1. customRoom temperature
  2. washthe solution was washed successively with saturated NaHCO3, H2O and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customto give the product (pale yellow oil)

Sources & evidence

ORD record
ord-d89a128c45c5421e93ed57c2778b7354
Source dataset
uspto-grants-2010_11
Patent number
US07834034B2

Reaction notes

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