1,2-Dibromoethane → HCID 18352878, compound

HRID 429812Notes

Reaction equation

HRID 429812 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1.BrCCBr.[Mg].Br[CH2:17][C:18]([CH3:20])=[CH2:19]>O1CCCC1>[CH3:19][C:18](=[CH2:17])[CH2:20][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1

Participants

6

Reactant 4

HCID 78391,2-DibromoethaneHCID 3577853-Bromo-2-methyl-1-propeneHCID 27761595-Bromo-2,3-dihydro-1-benzofuranHCID 5462224Magnesium

Product 1

HCID 18352878HCID 18352878, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
30 °C

Procedure

A solution of 5-bromo-2,3-dihydrobenzofuran (50 grams, 0.251 mole), and 1,2-dibromoethane (2.2 ml) in tetrahydrofuran (250 ml) was added dropwise to a stirred suspension of magnesium turnings (7.5 grams, 0.31 gram-atoms) in tetrahydrofuran (50 ml) over a period of 45 minutes. During the addition the reaction temperature was maintained at 30° C. The solution was cooled in an ice-bath and 3-bromo-2-methylpropene was added all at once. After stirring overnight, the reaction was quenched with cold 2% hydrochloric acid and the mixture was extracted with ether. Evaporation of solvent gave 5-(2-methylallyl)-2,3-dihydrobenzofuran as an oil (43.4 grams, 99%). M+ 174.

Workup

  1. additionDuring the addition the reaction temperature
  2. temperatureThe solution was cooled in an ice-bath
  3. customthe reaction was quenched with cold 2% hydrochloric acid
  4. extractionthe mixture was extracted with ether
  5. customEvaporation of solvent

Sources & evidence

ORD record
ord-a45ae6faff8c4257abb268f24372f7f0
Source dataset
uspto-grants-2001_11
Patent number
US06319920B1

Reaction notes

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