Water → 1-Bromo-3-((4-(difluoromethoxy)phenyl)ethynyl)benzene

HRID 2241012Notes

Reaction equation

HRID 2241012 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[CH:9])[CH:3]=1.CN(C=O)C.I[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH:23]([F:25])[F:24])=[CH:18][CH:17]=1.O>CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[C:9][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH:23]([F:25])[F:24])=[CH:18][CH:17]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 27370081-(Difluoromethoxy)-4-iodobenzeneHCID 114808181-Bromo-3-ethynylbenzene

Product 1

HCID 597903321-Bromo-3-((4-(difluoromethoxy)phenyl)ethynyl)benzene

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1-bromo-3-ethynylbenzene (9.1 g, 50.26 mmol), TEA (22.38 g, 30.8 mL, 221.1 mmol), PdCl2(ACN)2 (1.41 g, 2.01 mmol) and DMF (60 mL) was added 4-iodo(difluoromethoxy)benzene (10.85 g, 40.21 mmol). The reaction mixture became warm after the addition was completed. The mixture was stirred for 4 h. Then it was poured into water and diluted with EtOAc. The aqueous layer was separated and extracted twice with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated onto 40 g Celite. Flash chromatography (SiO2, Hexanes) provided 12 g, 92%, of the title compound as a yellow oil that crystallized into a yellow solid upon standing.

Workup

  1. temperatureThe reaction mixture became warm
  2. additionafter the addition
  3. customThe aqueous layer was separated
  4. extractionextracted twice with EtOAc
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated onto 40 g Celite
  8. customFlash chromatography (SiO2, Hexanes) provided 12 g, 92%
  9. customof the title compound as a yellow oil that crystallized into a yellow solid

Sources & evidence

ORD record
ord-92121d58d1d94b39990c9a0300322426
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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