Hydrogen Bromide → 2-Bromo-1-oxoindan-5-carbonitrile

HRID 1977817Notes

Reaction equation

HRID 1977817 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]#[N:12])=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[BrH:13].BrBr.S(=O)(O)[O-].[Na+]>C(O)(=O)C.O>[Br:13][CH:3]1[CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[C:7]([C:11]#[N:12])[CH:6]=2)[C:2]1=[O:1]

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 24408BromineHCID 3128961-oxo-2,3-dihydro-1H-indene-5-carbonitrileHCID 23665763Sodium Bisulfite

Product 1

HCID 184072382-Bromo-1-oxoindan-5-carbonitrile

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

3.93 g of 1-oxoindane-5-carbonitrile are dissolved in 40 ml of glacial acetic acid and, after addition of 0.1 ml of hydrobromic acid (48% strength in water), at room temperature a solution of 1.34 ml of bromine in 8 ml of acetic acid is added dropwise. The reaction mixture is stirred at room temperature for 3 h and then added to a mixture of 20 g of ice and 40 g of water, 0.5 g of sodium bisulfite is added and the mixture is extracted by shaking twice with 50 ml of dichloromethane each time. The organic phase is washed with 50 ml of water, dried over magnesium sulfate, concentrated in vacuo and chromatographed on silica gel with toluene/ethyl acetate 25/1. 2-Bromo-l-oxoindane-5-carbonitrile is obtained with a melting point of 115-118° C.

Workup

  1. additionis added
  2. extractionthe mixture is extracted
  3. stirringby shaking twice with 50 ml of dichloromethane each time
  4. washThe organic phase is washed with 50 ml of water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customchromatographed on silica gel with toluene/ethyl acetate 25/1

Sources & evidence

ORD record
ord-f8696b3e7928485790581e7349f8ee66
Source dataset
uspto-grants-2001_05
Patent number
US06235763B1

Reaction notes

Loading…