Toluene → 4-Fluorophenylethynyl bromide

HRID 1400608Notes

Reaction equation

HRID 1400608 reaction equation
[Br:1][C:2](Br)=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][CH:5]=1.CC(C)([O-])C.[K+].C1(C)C=CC=CC=1>O>[Br:1][C:2]#[C:3][C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 114601591-(2,2-Dibromovinyl)-4-fluorobenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 111483184-Fluorophenylethynyl bromideYield 70.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-(2,2-dibromo-vinyl)-4-fluoro-benzene (0.6 g, 0.00214 mol), potassium tertbutoxide (0.48 g, 0.00428 mol) and toluene (6 mL) were heated at 80° C. for 4 h. After completion of reaction, the reaction mixture was cooled to RT, diluted with water (15 mL), and extracted with EtOAc (3×50 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduce pressure to obtain product as a yellow oil (0.3 g, 70%).

Workup

  1. customAfter completion of reaction
  2. temperaturethe reaction mixture was cooled to RT
  3. extractionextracted with EtOAc (3×50 mL)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9a7264e49c034c63879e621c8555949c
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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