Sodium Carbonate → 4'-Trifluoromethyl-biphenyl-3-carboxylic acid

HRID 1993020Notes

Reaction equation

HRID 1993020 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18]([OH:20])=[O:19].C([O-])([O-])=O.[Na+].[Na+]>CC(O)C.O.[Pd]>[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6]([C:15]2[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=2)[C:18]([OH:20])=[O:19])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 114563-Bromobenzoic acidHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 27827184'-Trifluoromethyl-biphenyl-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21889133Propan-2-ol--water (1/1)Solvent

Conditions

Temperature
70 °C

Procedure

The Suzuki coupling was carried out according to the method of Dyer et al. (2001) Tetrahedron Letters 42: 1765-1767. Commercially available 4-(Trifluoromethyl)phenylboronic acid (15 g, 78.7 mmol) and 3-bromobenzoic acid (15.1 g, 75 mmol) were suspended in 2-propanol:water (1:4, 72 mL). 10% Pd/C (1.5 g) was added followed by aqueous Na2CO3 (39 mL, 20% by wt.). The resulting mixture was heated at 70° C. for 4 hours. The precipitate was filtered and rinsed with 20% aqueous Na2CO3 solution. The filtrate was diluted with water and acidified to pH=2. The white solid was filtered and dried in vacuo. The crude material (2.1) (19.69 g) was used in the next step without further purification.

Workup

  1. filtrationThe precipitate was filtered
  2. washrinsed with 20% aqueous Na2CO3 solution
  3. additionThe filtrate was diluted with water
  4. filtrationThe white solid was filtered
  5. customdried in vacuo
  6. customThe crude material (2.1) (19.69 g) was used in the next step without further purification

Sources & evidence

ORD record
ord-19c93ee9d7624dcdb5ea71b16a7096d6
Source dataset
uspto-grants-2010_01
Patent number
US07649110B2

Reaction notes

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