Dichloromethane → HCID 22148544, compound

HRID 1823942Notes

Reaction equation

HRID 1823942 reaction equation
Br[C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C(Cl)Cl>COCCOC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:9]1[CH:2]=[C:3]([CH:6]=[CH:7][C:8]=1[F:10])[CH:4]=[O:5]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 27343222-Chlorophenylboronic acidHCID 27733192-Bromo-4-fluorobenzaldehyde

Product 1

HCID 22148544HCID 22148544, compoundYield 54.1%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-bromo-4-fluorobenzaldehyde (2.0 g, 9.85 mmol) and 2-chlorophenylboronic acid (2.0 g, 12.1 mmol) in ethylene glycol dimethyl ether (20 mL) is added 2N sodium carbonate (19.7 mL) followed by tetrakis(triphenylphosphine) palladium (0) (573 mg, 0.50 mmol). The reaction is subsequently stirred at 80° C. for 4 hours under an argon atmosphere. Once complete, the reaction mixture is poured into CH2Cl2 and water is added. The organic layer is separated, dried over sodium sulfate and concentrated to provide a crude oil. The crude product is purified by column chromatography (10% ethyl acetate in hexanes) to afford 1.25 g of 3-(2-chlorophenyl)-4-fluorobenzaldehyde.

Workup

  1. additionis added
  2. customThe organic layer is separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customto provide a crude oil
  6. customThe crude product is purified by column chromatography (10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-659cbaad6eeb482eaf1cf2d3fde759eb
Source dataset
uspto-grants-2006_05
Patent number
US07041690B2

Reaction notes

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