Carbon Dioxide → 2-Bromo-6-chlorobenzoic acid

HRID 271319Notes

Reaction equation

HRID 271319 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([Cl:8])[CH:5]=[CH:6][CH:7]=1.CCCCCCC.C([N-]C(C)C)(C)C.[Li+].O1CCCC1.C(C1C=CC=CC=1)C.[C:37](=[O:39])=[O:38]>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:37]([OH:39])=[O:38]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 79281-Bromo-3-chlorobenzeneHCID 86590273LDA THF ethylbenzene heptane

Product 1

HCID 331252-Bromo-6-chlorobenzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

The mixture of 500 mg of 3-bromochlorobenzen and 3 ml of tetrahydrofuran was cooled down to −78° C. and 1.3 ml of 2.0M lithium diisopropylamide heptane/tetrahydrofuran/ethylbenzene solution was added. After stirring it for 2 hours, the mixture was put into dry ice and washed and extracted as described in Referencial Example 1 to obtain a crude material. The crude material was washed with a mixed solvent of hexane-ethyl acetate to obtain the title compound.

Workup

  1. washwashed
  2. extractionextracted
  3. customto obtain a crude material
  4. washThe crude material was washed with a mixed solvent of hexane-ethyl acetate

Sources & evidence

ORD record
ord-7423d2f378814025aaaf5b359643aee7
Source dataset
uspto-grants-2008_11
Patent number
US07452905B2

Reaction notes

Loading…