Water → 1-(2-Bromoethyl)-3-methylindole

HRID 596952Notes

Reaction equation

HRID 596952 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:11][CH2:12]O)[CH:3]=1.P(Br)(Br)[Br:15].O>CCOCC>[Br:15][CH2:12][CH2:11][N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]([CH3:1])=[CH:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 122267423-Methylindole-1-ethanol

Product 1

HCID 213895541-(2-Bromoethyl)-3-methylindole

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of 7.2 g of 3-methylindole-1-ethanol, described in Example 1, in 500 ml. of dry ether (ice bath) is slowly added 1.2 ml of phosphorus tribromide in 100 ml of dry ether. A dark red oily complex separates. The reaction mixture is stirred 36-48 hours at room temperature, then decomposed with ice and water. The separated ether-layer is quickly washed with a 10% solution of sodium bicarbonate and with water again, dried over calcium chloride for 2 min., decanted, and dried over magnesium sulfate for 30 min. The filtrate is evaporated yielding 1-(2-bromoethyl)-3-methylindole.

Workup

  1. washThe separated ether-layer is quickly washed with a 10% solution of sodium bicarbonate and with water again
  2. dry with materialdried over calcium chloride for 2 min.
  3. customdecanted
  4. dry with materialdried over magnesium sulfate for 30 min
  5. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-5a50ab763c364b90ba50e245e9f78ee4
Source dataset
uspto-grants-1977_03
Patent number
US04012511

Reaction notes

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