Hydrogen Bromide → HCID 59750636, compound

HRID 422223Notes

Reaction equation

HRID 422223 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][CH:7]([CH2:12][OH:13])[CH2:6]2.Br>>[OH:13][CH2:12][CH:7]1[CH2:6][C:5]2[C:9](=[CH:10][CH:11]=[C:3]([OH:2])[CH:4]=2)[CH2:8]1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 230442542,3-Dihydro-5-methoxy-1H-indene-2-methanol

Product 1

HCID 59750636HCID 59750636, compoundYield 63.1%

Procedure

Combine (5-Methoxy-indan-2-yl)-methanol (117.0 mg, 0.65 mmol), and 48% HBr (aq). After the reaction refluxes for 30 minutes, cool to room temperature and extract the product with ethyl acetate. Wash with brine and dry over Na2SO4. After concentrating the organic layer under reduced pressure, flash chromatograph using 2/1 Hexanes/Ethyl acetate eluent to afford 67.3 mg, 0.41 mmol (63% yield) of the title compound: 1H NMR (500 MHz, CDCl3); 2.6-2.8 (3H, m), 2.9-3.1 (2H, m), 3.6-3.8 (2H, m), 6.6-6.8 (2H, m), 7.0-7.1 (1H, m); TLC 1:1 Hexanes:Ethyl acetate Rf:=0.3.

Workup

  1. extractionextract the product with ethyl acetate
  2. washWash with brine
  3. dry with materialdry over Na2SO4
  4. concentrationAfter concentrating the organic layer under reduced pressure, flash chromatograph

Sources & evidence

ORD record
ord-de1a749bb62e4ad0b3e90500877e5a8b
Source dataset
uspto-grants-2012_01
Patent number
US08101638B2

Reaction notes

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