Toluene → 3'-(Trifluoromethoxy)[1,1'-biphenyl]-4-carbaldehyde

HRID 1470609Notes

Reaction equation

HRID 1470609 reaction equation
C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].Br[C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1.[F:23][C:24]([F:36])([F:35])[O:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1>O>[F:23][C:24]([F:35])([F:36])[O:25][C:26]1[CH:31]=[C:30]([C:15]2[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=2)[CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 707414-BromobenzaldehydeHCID 27343853-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride)

Product 1

HCID 534038293'-(Trifluoromethoxy)[1,1'-biphenyl]-4-carbaldehydeYield 80.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of toluene (35 mL) and water (5 mL) was degassed with nitrogen for 30 minutes. A mixture of sodium carbonate (1.9 g, 18.09 mmol), 4-bromobenzaldehyde (0.7 g, 3.72 mmol), 3-trifluoromethoxyphenylboronic acid (2.86 g, 4.78 mmol) and tetrakis triphenyl phosphene palladium(0) (0.9 g, 0.75 mmol) was added to the above degassed water/toluene mixture. The reaction mixture was refluxed overnight. After the reaction is completed it was cooled to room temperature and extracted with ethyl acetate. The combined organic layers were dried over sodium sulphate and concentrated. The resulting residue was purified by column chromatography using 5% ethyl acetate in hexane to obtain the title compound (0.8 g, 80%).

Workup

  1. customwas degassed with nitrogen for 30 minutes
  2. additionwas added to the
  3. customabove degassed water/toluene mixture
  4. temperatureThe reaction mixture was refluxed overnight
  5. extractionextracted with ethyl acetate
  6. dry with materialThe combined organic layers were dried over sodium sulphate
  7. concentrationconcentrated
  8. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-bed691173f454ac0a4db4cce96ceacc5
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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