Carbon Dioxide → 2,3-Dichloro-6-iodobenzoic acid

HRID 2287342

Reaction equation

HRID 2287342 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([I:20])=[CH:16][C:15]=1[Cl:21].[C:22](=[O:24])=[O:23]>C1COCC1.O>[Cl:21][C:15]1[C:14]([Cl:13])=[CH:19][CH:18]=[C:17]([I:20])[C:16]=1[C:22]([OH:24])=[O:23]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 7912DiisopropylamineHCID 88591Benzene, 1,2-dichloro-4-iodo-HCID 178418339Butyllithium

Product 1

HCID 220088162,3-Dichloro-6-iodobenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

n-Butyllithium (1.45M solution in hexane, 19.4 mmol, 13.4 ml) was added dropwise to a stirred solution of diisopropylamine (21.4 mmol, 3.0 ml) in THF (90 ml) at 0° C. After 30 minutes, the solution was cooled to -78° C. and a solution of 1,2-dichloro-4-iodobenzene (5.30 g, 19.4 mmol) in THF (10 ml) was added dropwise. After 10 minutes, solid carbon dioxide was added cautiously and the mixture allowed to warm to room temperature over 16 h. The mixture was diluted with water and extracted twice with ethyl acetate. The aqueous layer was acidified with dilute aqueous hydrochloric acid and then extracted twice with ethyl acetate. The extracts were dried over sodium sulphate and evaporated to give the title compound as a yellow solid (3.59 g). 300 MHz 1H NMR (d6 -DMSO) 11.5 (1H, br.s), 7.82 (1H, d, J 8.4 Hz), 7.44 (1H, d, J 8.4 Hz).

Workup

  1. waitAfter 10 minutes
  2. temperatureto warm to room temperature over 16 h
  3. extractionextracted twice with ethyl acetate
  4. extractionextracted twice with ethyl acetate
  5. dry with materialThe extracts were dried over sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-d2ed216781954c6087de00a3368607ae
Source dataset
uspto-grants-2000_07
Patent number
US06083952

Linked notes

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