Toluene → HCID 59455074, compound

HRID 1401677Notes

Reaction equation

HRID 1401677 reaction equation
[Br:1][C:2](Br)=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([F:12])[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]([O:10][CH3:11])=[C:6]([F:12])[CH:5]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 23665647Potassium tert-butoxideHCID 594550774-(2,2-Dibromovinyl)-2-fluoro-1-methoxybenzene

Product 1

HCID 59455074HCID 59455074, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-(2,2-dibromo-vinyl)-3-fluoro-4-methoxybenzene (0.5 g, 0.00161 mol), potassium tertbutoxide (0.36 g, 0.00322 mol) and toluene (6 mL) were heated at 80° C. for 4 h. After completion, 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, 81%).

Workup

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

Sources & evidence

ORD record
ord-cea7bcb63f7a4d42b0f2621ee32dd939
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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