Carbon Dioxide → 3,5-Dibromo-2-fluorobenzoic acid

HRID 1612449Notes

Reaction equation

HRID 1612449 reaction equation
C([Li])CCC.CC1(C)CCCC(C)(C)N1.[Br:16][C:17]1[CH:22]=[C:21]([Br:23])[CH:20]=[CH:19][C:18]=1[F:24].[C:25](=[O:27])=[O:26]>C1COCC1.O.[OH-].[Na+]>[Br:16][C:17]1[C:18]([F:24])=[C:19]([CH:20]=[C:21]([Br:23])[CH:22]=1)[C:25]([OH:27])=[O:26]

Participants

8

Reactant 4

HCID 280Carbon DioxideHCID 130352,2,6,6-TetramethylpiperidineHCID 150342,4-Dibromo-1-fluorobenzeneHCID 178418339Butyllithium

Product 1

HCID 27739703,5-Dibromo-2-fluorobenzoic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

Butyllithium (1.6M solution in hexanes, 12.3 ml, 19.7 mmol) was added dropwise to a solution of 2,2,6,6-tetramethylpiperidine (3.32 ml, 19.7 mmol) in THF at −78° C. The reaction was stirred for 10 min. prior to the addition of 2,4-dibromofluorobenzene (5 g, 19.7 mmol). Stirring was continued for 2 h. The solution was then poured onto freshly crushed dry ice and allowed to warm to room temperature. The resulting solution was diluted with water (100 ml) and NaOH (2M, 10 ml) was added. This was extracted with ether (2×) and the aqueous layer was acidified to pH 1 (2M HCl) to afford a gummy solid which was triturated from ether to afford the title compound (D37) as a colourless solid (1.23 g).

Workup

  1. stirringStirring
  2. waitwas continued for 2 h
  3. additionwas added
  4. extractionThis was extracted with ether (2×)
  5. customto afford a gummy solid which
  6. customwas triturated from ether

Sources & evidence

ORD record
ord-4008d10acd9840fb96733d4a9e4645be
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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