Carbon Dioxide → 5-Chloro-2-fluoro-4-methylbenzoic acid

HRID 1849586Notes

Reaction equation

HRID 1849586 reaction equation
Br[C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([CH3:9])=[CH:4][C:3]=1[F:10].C([Mg]Cl)(C)C.[C:16](=[O:18])=[O:17]>C1COCC1>[Cl:8][C:6]1[C:5]([CH3:9])=[CH:4][C:3]([F:10])=[C:2]([CH:7]=1)[C:16]([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 27362284-Bromo-2-chloro-5-fluorotolueneHCID 178418918HCID 178418918, compound

Product 1

HCID 580424465-Chloro-2-fluoro-4-methylbenzoic acidYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-bromo-5-chloro-2-fluoro-4-methylbenzene (11.3 g, 50 mmol) in dry THF (100 mL) was added isopropylmagnesium chloride (30 mL, 2 M) dropwise. After stirring at room temperature for 30 min, dry CO2 was added and the mixture was stirred at room temperature for additional 30 min. The reaction was quenched by sat. NH4Cl and extracted with EtOAc (100 mL×3). The combined organic layers were washed with water (50 mL×3), dried over anhydrous Na2SO4, filtered and concentrated to give the desired product (4.7 g, 49%). LCMS (ESI) m/z: 187.0 [M−H]−.

Workup

  1. stirringthe mixture was stirred at room temperature for additional 30 min
  2. customThe reaction was quenched by sat. NH4Cl
  3. extractionextracted with EtOAc (100 mL×3)
  4. washThe combined organic layers were washed with water (50 mL×3)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-cbf9b1652e0d42c594cefc7cb46bb460
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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