Methanol → HCID 59173400, compound

HRID 220095Notes

Reaction equation

HRID 220095 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:11]=[C:12]([CH:14]=C)[CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7].C[OH:19]>>[CH:14]([C:12]1[CH:11]=[C:5]([CH:4]=[C:3]([C:2]([F:17])([F:16])[F:1])[CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[O:19]

Participants

3

Reactant 2

HCID 887MethanolHCID 59173387Ethyl 3-ethenyl-5-(trifluoromethyl)benzoate

Product 1

HCID 59173400HCID 59173400, compound

Conditions

Temperature
-78 °C

Procedure

25.39 g (103.96 mmol) of ethyl 3-(trifluoromethyl)-5-vinylbenzoate 33 is dissolved in dry MeOH (200 mL) and reaction vessel Is cooled down to −78° C. Then O3 is bubbled through for 1.5 hours until the reaction mixture turned dark blue. Then ozone is turned off and nitrogen is bubbled through the reaction mixture to remove extra ozone from the solution. 9.6 g of dimethyl sufide (155.95 mmol, 1.5 eq) is added and the reaction mixture is stirred at −78° C. for 2 hours followed by at room temperature for another hour. All the solvents are removed and ethyl 3-formyl-5-(trifluoromethyl)benzoate 34 is isolated via flash column chromatography (5-10% EtOAc/Hex). MS: m/z [M+H+]) 247.18, 1H NMR 10.16 (s, 1H), 8.73 (s, 1H), 8.56, (s, 1H), 8.35 (s, 1H), 4.46-4.51 (q, 2H, J=7.21 Hz), 1.45-1.49 (t, 3H, J=7.21 Hz).

Workup

  1. customreaction vessel
  2. customThen O3 is bubbled through for 1.5 hours until the reaction mixture
  3. customnitrogen is bubbled through the reaction mixture
  4. customto remove extra ozone from the solution
  5. addition9.6 g of dimethyl sufide (155.95 mmol, 1.5 eq) is added
  6. waitfollowed by at room temperature for another hour
  7. customAll the solvents are removed

Sources & evidence

ORD record
ord-709e1f68a4d047c18ed2d0876545f1db
Source dataset
uspto-grants-2012_06
Patent number
US08202876B2

Reaction notes

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