Water → 4'-(Trifluoromethyl)-4-biphenylcarbaldehyde

HRID 1767142Notes

Reaction equation

HRID 1767142 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[F:10][C:11]([F:22])([F:21])[C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+].O>[Pd].C(O)(C)C>[F:10][C:11]([F:22])([F:21])[C:12]1[CH:17]=[CH:16][C:15]([C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 707414-BromobenzaldehydeHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 27827124'-(Trifluoromethyl)-4-biphenylcarbaldehydeYield 85.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 3776IsopropanolSolvent

Conditions

Temperature
81.5 °C

Procedure

5% Palladium on carbon, type 58, 50% paste (0.94 kg, 0.22 moles Pd) was added to a mixture of 4-bromobenzaldehyde (3.34 kg, 17.69 moles), 4-trifluoromethylphenyl boronic acid (3.50 kg, 18.06 moles) and sodium carbonate (3.75 kg, 35.38 moles) in process water (36 L). Isopropanol (36 L) was added and the resultant mixture heated to reflux (80-83° C.) for ca. 2.5 hours. The catalyst was removed from the hot suspension by filtration through celite (1.5 kg). The celite bed was washed with a hot (ca. 70° C.) isopropanol (10 L)/water (10 L) mixture then the combined filtrate and wash were cooled to 23° C., process water (18 L) was added and the mixture stirred at 20-25° C. for ca. 17.5 hours. The solid was collected by filtration, washed with process water (1×27 L, 2×18 L) then dried at 39° C. for 24 hours to give the title compound (3.78 kg, 85%) as a white solid. 1H NMR (CDCl3) δ 7.75 (4H, s), 7.78 (2H, d) 7.98 (2H, d), 10.10 (1H, s)

Workup

  1. customThe catalyst was removed from the hot suspension by filtration through celite (1.5 kg)
  2. washThe celite bed was washed with a hot (ca. 70° C.) isopropanol (10 L)/water (10 L) mixture
  3. washthe combined filtrate and wash
  4. temperaturewere cooled to 23° C.
  5. additionprocess water (18 L) was added
  6. filtrationThe solid was collected by filtration
  7. washwashed with process water (1×27 L, 2×18 L)
  8. customthen dried at 39° C. for 24 hours

Sources & evidence

ORD record
ord-20c448542d424e5a9e45c511cbf61db6
Source dataset
uspto-grants-2007_06
Patent number
US07232902B2

Reaction notes

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