Carbon Dioxide → 2-Chlorobiphenyl-4-carboxylic acid

HRID 1777337Notes

Reaction equation

HRID 1777337 reaction equation
II.[Mg].Br[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:7]([Cl:17])[CH:6]=1.[C:18](=[O:20])=[O:19].Cl>O1CCCC1>[Cl:17][C:7]1[CH:6]=[C:5]([C:18]([OH:20])=[O:19])[CH:10]=[CH:9][C:8]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 807IodineHCID 5462224MagnesiumHCID 134574164-Bromo-2-chlorobiphenyl

Product 1

HCID 198789252-Chlorobiphenyl-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
65 °C

Procedure

Few crystals of iodine are added to tetrahydrofuran (200 mL) containing magnesium turnings (2.8 g, 0.117 mol). The mixture is heated at 60-70° C. A solution of 4-bromo-2-chlorobiphenyl (26 g, 0.097 mol) in tetrahydrofuran (50 mL) is added dropwise to the reaction mixture and refluxed for 1 hr. Reaction mixture is brought to room temperature and then cooled to −20° C. Carbon dioxide gas is passed through the reaction mixture for 45 minutes. The reaction mixture is treated with 3N HCl (125 mL) and extracted with ethyl acetate (2×200 mL). Combined organic layer is dried over sodium sulphate. Removal of solvent under reduced pressure gives a solid which is washed with diethyl ether (2×100 mL) and then dried to furnish 2-chlorobiphenyl-4-carboxylic acid.

Workup

  1. temperaturerefluxed for 1 hr
  2. customReaction mixture
  3. customis brought to room temperature
  4. temperaturecooled to −20° C
  5. extractionextracted with ethyl acetate (2×200 mL)
  6. dry with materialCombined organic layer is dried over sodium sulphate
  7. customRemoval of solvent under reduced pressure
  8. customgives a solid which
  9. washis washed with diethyl ether (2×100 mL)
  10. customdried

Sources & evidence

ORD record
ord-b6bf6c8b7996428abae041946a896b75
Source dataset
uspto-grants-2016_02
Patent number
US09266867B2

Reaction notes

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