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

HRID 2375727Notes

Reaction equation

HRID 2375727 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 acidYield 98.6%

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 i-PrOH: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 to afford 2.1 (19.69 g).

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

Sources & evidence

ORD record
ord-a2e0a31065ed4727999dfc6e76d4dcf6
Source dataset
uspto-grants-2008_12
Patent number
US07465804B2

Reaction notes

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