Sodium Carbonate → 2-(4-Formyl-2-methoxy-phenoxy)4-trifluoromethyl-benzonitrile

HRID 1178535Notes

Reaction equation

HRID 1178535 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[CH:21]=[O:22])[O:5][C:6]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:7]=1[C:8]#[N:9].C1(B(O)O)C=CC=CC=1.[C:32](=O)([O-])[O-:33].[Na+].[Na+]>C(COC)OC.[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O.C(O)C>[CH:21]([C:20]1[CH:19]=[CH:18][C:4]([O:5][C:6]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:7]=2[C:8]#[N:9])=[C:3]([O:33][CH3:32])[CH:2]=1)=[O:22]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 219303412-(3-Bromo-4-formyl-phenoxy)-4-trifluoromethyl-benzonitrile

Product 1

HCID 219304562-(4-Formyl-2-methoxy-phenoxy)4-trifluoromethyl-benzonitrileYield 14%

Reagents, catalysts & solvents 4

HCID 178506421HCID 178506421, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

Under nitrogen, 2-(3-bromo-4-formyl-phenoxy)-4-trifluoromethyl-benzonitrile (0.87 g, 2.6 mmol), phenylboronic acid (336 mg, 2.7 mmol), 1,1′-bis(diphenyl)phosphino-ferrocene palladium (9 mg, 0.13 mmol) and sodium carbonate (331 mg, 3.1 mmol) in dimethoxyethane:water:ethanol solution (7:3:2, 10 mL) was stirred at 60° C. for 6 h and then at 40° C. for 16 h. The mixture was then poured over water, extracted into ethyl acetate, and dried over MgSO4. The crude material was chromatographed on an ISCO CombiFlash Chromatography System to yield 2-(4-formyl-2-methoxy-phenoxy)-4-trifluoromethyl-benzonitrile as a clear oil (117 mg, 14%).

Workup

  1. extractionextracted into ethyl acetate
  2. dry with materialdried over MgSO4
  3. customThe crude material was chromatographed on an ISCO CombiFlash Chromatography System

Sources & evidence

ORD record
ord-d35b9e39d2ce4c00ba82e751e24b9cf3
Source dataset
uspto-grants-2007_10
Patent number
US07276528B2

Reaction notes

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