1-Bromo-2-ethylbenzene → HCID 93510923, compound

HRID 1771420Notes

Reaction equation

HRID 1771420 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH3:9].[Li][CH2:11][CH2:12][CH2:13][CH3:14].[O:15]1[C@H](CC)C1>C1COCC1>[CH2:13]([C:12]1[CH:11]=[CH:4][CH:5]=[CH:6][C:7]=1[C@H:2]([OH:15])[CH2:3][CH2:8][CH3:9])[CH3:14]

Participants

5

Reactant 3

HCID 160891-Bromo-2-ethylbenzeneHCID 11147670(2R)-2-EthyloxiraneHCID 178418339Butyllithium

Product 1

HCID 93510923HCID 93510923, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

The 1-bromo-2-ethylbenzene (2.0 g) was dissolved in dry THF and the mixture was cooled to −78° C. 1.6 M n-BuLi (20.26 ml) was slowly added to the reaction mixture and then the mixture was stirred at −78° C. After 1 h (R)-(+)-1,2-epoxybutane (1.1 g) was added in 10 ml of THF. The reaction mixture was allowed to warm to ambient temperature and then stirred over night. The reaction was quenched with ice-water and product extracted in heptanes, and finally purified by using the separation method E yielding the title compound (1.1 g).

Workup

  1. temperatureto warm to ambient temperature
  2. stirringstirred over night
  3. customThe reaction was quenched with ice-water and product
  4. extractionextracted in heptanes
  5. customfinally purified
  6. customthe separation method E

Sources & evidence

ORD record
ord-01c265e2467949fd9ee20c95a63f0c7b
Source dataset
uspto-grants-2016_02
Patent number
US09249127B2

Reaction notes

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