Toluene → 4-Biphenylcarboxylic acid, 4'-chloro-

HRID 1242800Notes

Reaction equation

HRID 1242800 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.I[C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(C)C=CC=CC=1>C(O)CCC.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 10796Cesium carbonateHCID 120854-Iodobenzoic acidHCID 742994-Chlorophenylboronic acid

Product 1

HCID 6160024-Biphenylcarboxylic acid, 4'-chloro-Yield 41%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

4-Chlorophenylboronic acid (501 mg) was combined with 4-iodobenzoic acid (795 mg), cesium carbonate (5.22 g), toluene (16 mL), water (8 mL) and n-butanol (4 mL). The mixture was degassed under vacuum with argon purging after which, tetrakis-triphenylphosphine palladium (40 mg) was added. The reaction was heated to 80° C. for 20 hours after which, it was cooled to room temperature and diluted with ethyl acetate (16 mL). The solids were collected on a Celite pad and washed with hot methanol. The methanol filtrate was concentrated to dryness giving 4′-chloro-4-biphenylcarboxylic acid (305 mg). Yield=41%

Workup

  1. customThe mixture was degassed under vacuum with argon purging after which, tetrakis-triphenylphosphine palladium (40 mg)
  2. additionwas added
  3. temperaturewas cooled to room temperature
  4. additiondiluted with ethyl acetate (16 mL)
  5. customThe solids were collected on a Celite pad
  6. washwashed with hot methanol
  7. concentrationThe methanol filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-1e3bf82385f142c3a777aa5e2486e965
Source dataset
uspto-grants-2006_10
Patent number
US07115741B2

Reaction notes

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