Toluene → 4'-Trifluoromethoxy-biphenyl-4-carbaldehyde

HRID 1470607Notes

Reaction equation

HRID 1470607 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:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1>O>[F:23][C:24]([F:35])([F:36])[O:25][C:26]1[CH:31]=[CH:30][C:29]([C:15]2[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=2)=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 707414-BromobenzaldehydeHCID 27343864-(Trifluoromethoxy)phenylboronic acid

Product 1

HCID 27607204'-Trifluoromethoxy-biphenyl-4-carbaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of toluene (70 mL) and water (10 mL) was degassed with nitrogen for 30 min. A mixture of sodium carbonate (3.2 g, 30.43 mmol), 4-bromobenzaldehyde (2.0 g, 10.6 mmol), 4-trifluoromethoxyphenylboronic acid (2.86 g, 13.95 mmol) and tetrakis triphenyl phosphene palladium(0) (1.0 g, 1.562 mmol) were added to the above degassed water/toluene mixture. The reaction mixture refluxed overnight. After the reaction is completed, the reaction mixture 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 3% ethyl acetate in hexane to obtain the title compound. 1H NMR (300 MHz, CDCl3): δ (ppm)=7.2-8.0 (m, 8H), 10.0 (s, 1H).

Workup

  1. customwas degassed with nitrogen for 30 min
  2. additionwere added to the
  3. customabove degassed water/toluene mixture
  4. temperatureThe reaction mixture 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-21ecc537d7b54f84b4dcc7c02ca2fdaf
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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