Allyl bromide → 38434-35-4

HRID 2298154Notes

Reaction equation

HRID 2298154 reaction equation
[CH:1]1([CH2:10][CH2:11]O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C([Br:16])C=C>C(#N)C>[CH:1]1([CH2:10][CH2:11][Br:16])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 7841Allyl bromideHCID 123228632-(2,3-Dihydro-1H-inden-1-yl)ethan-1-ol

Product 1

HCID 1232286838434-35-4Yield 91.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N,N-Carbonyl diimidazole (2.0 g, 12.3 mmol) was added to a solution of 2-indanylethanol (2.0 g, 12.3 mmol) in acetonitrile. The reaction mixture was stirred at room temperature for 1 h and allyl bromide (8.93 g, 73.8 mmol) was added. The reaction mixture was heated to 70° C. for 24 h and was poured onto water. The aqueous solution was extracted with Et2O and the organic solution was washed with water (1×) followed by brine (1×). The organic solution was dried over MgSO4, filtered, and concentrated to afford the title compound (2.54 g). 1H NMR (400 MHz, CDCl3) δ 7.10-7.25 (m, 4H), 3.48 (t, 2H), 3.11 (m, 2H), 2.63 (m, 3H), 2.07 (m, 2H).

Workup

  1. temperatureThe reaction mixture was heated to 70° C. for 24 h
  2. additionwas poured onto water
  3. extractionThe aqueous solution was extracted with Et2O
  4. washthe organic solution was washed with water (1×)
  5. dry with materialThe organic solution was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b91c560948ca4dc9b4bf25c51bc1c34a
Source dataset
uspto-grants-2002_12
Patent number
US06492412B2

Reaction notes

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