Sulfuric Acid → HCID 66642876, compound

HRID 1170951Notes

Reaction equation

HRID 1170951 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([F:10])[CH:3]=1.[CH3:11][CH:12](O)[CH3:13].OS(O)(=O)=O>>[Br:1][C:2]1[CH:3]=[C:4]([F:10])[C:5]([O:8][CH3:9])=[C:6]([CH:12]([CH3:13])[CH3:11])[CH:7]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 753784-Bromo-2-fluoroanisole

Product 1

HCID 66642876HCID 66642876, compoundYield 38.4%

Conditions

Temperature
80 °C

Procedure

To a mixture of 4-bromo-2-fluoroanisole (2.0 g, 9.70 mmol) and 2-propanol (1.2 g, 19.4 mmol) at room temperature was added 80% H2SO4 (10.0 mL). The reaction mixture was heated at 80° C. for 12 h, cooled to room temperature, quenched with ice (50 g) and extracted with ether (20 mL×2). The combined organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel, eluting with 5% ethyl acetate in hexanes to afford 4-bromo-6-fluoro-2-iso-propylanisole (0.92 g, 38%): 1H NMR (300 MHz, CD3OD): δ 7.36 (d, J=10.5 Hz, 1 H), 7.22 (d, J=10.5 Hz, 1 H), 3.91 (s, 3 H), 3.24 (m, 1 H), 1.26 (d, J=6.6 Hz, 6 H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=ethyl acetate-hexanes (5:95); Rf=0.50.

Workup

  1. temperaturecooled to room temperature
  2. customquenched with ice (50 g)
  3. extractionextracted with ether (20 mL×2)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography on silica gel
  8. washeluting with 5% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-dd64a566c3434e46b1c9db2f606ffcdd
Source dataset
uspto-grants-2010_11
Patent number
US07829552B2

Reaction notes

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