Hydrochloric Acid → 2-Methyl-3,4,6-trifluorobenzoic acid

HRID 2271267Notes

Reaction equation

HRID 2271267 reaction equation
F[C:2]1[C:10]([F:11])=[C:9]([F:12])[CH:8]=[C:7]([F:13])[C:3]=1[C:4]([OH:6])=[O:5].[CH3:14][Mg]Br.C(OCC)C.O.Cl>C(OCC)C>[F:11][C:10]1[C:2]([CH3:14])=[C:3]([C:7]([F:13])=[CH:8][C:9]=1[F:12])[C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 27765912,3,4,6-tetrafluorobenzoic AcidHCID 178467822HCID 178467822, compound

Product 1

HCID 101303052-Methyl-3,4,6-trifluorobenzoic acidYield 92%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-10 °C

Procedure

200 mg of 2,3,4,6-tetrafluorobenzoic acid was dissolved in 10 ml of diethyl ether and cooled to −10° C. in an argon atmosphere. Then 1.72 ml of a methyl magnesium bromide-diethyl ether solution (3 moles/liter) was added dropwise. After completion of dropwise addition, the reaction mixture was heated to room temperature and stirred at room temperature for 17 hours. The reaction mixture was added to about 50 ml of cold water and adjusted to pH 1 with concentrated hydrochloric acid. The reaction mixture was extracted with ethyl acetate and separated into liquids. The organic layer was separated, dried over anhydrous sodium sulfate and concentrated to give 181 mg of 3,4,6-trifluoro-2-methylbenzoic acid (yield: 92%).

Workup

  1. additionAfter completion of dropwise addition
  2. temperaturethe reaction mixture was heated to room temperature
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. customseparated into liquids
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1ef3267c7d5040f4a6380bce86b3c544
Source dataset
uspto-grants-2001_12
Patent number
US06333431B1

Reaction notes

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