Boron tribromide → 5,6-Dihydroxy-2,3-dihydro-1H-inden-1-one

HRID 2252248Notes

Reaction equation

HRID 2252248 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12]C)[C:8](=[O:14])[CH2:7][CH2:6]2.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[OH:12])[C:8](=[O:14])[CH2:7][CH2:6]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 750185,6-Dimethoxy-1-indanone

Product 1

HCID 115934875,6-Dihydroxy-2,3-dihydro-1H-inden-1-oneYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5,6-dimethoxy-indan-1-one (40.0 g, 0.208 mol) in CH2Cl2 (800 mL) at −78° C. was added BBr3 (59.0 mL, 0.624 mol) dropwise. The dry ice bath was removed after the addition. The mixture was stirred at room temperature for 1 hour and poured into a large amount of ice/water and stirred vigorously. The pink solid was filtered, washed with water, and vacuum oven dried to give 33.3 g (98%) of the desired product. MS (DCI/NH3) m/z: 165.0 (M+H)+; 1H NMR (300 MHz, CD3OD) δ ppm 2.58-2.61 (m, 2H) 2.98 (t, J=5.55 Hz, 2H) 6.85 (s, 1H) 7.04 (s, 1H).

Workup

  1. customThe dry ice bath was removed
  2. additionafter the addition
  3. additionpoured into a large amount of ice/water
  4. stirringstirred vigorously
  5. filtrationThe pink solid was filtered
  6. washwashed with water, and vacuum oven
  7. customdried

Sources & evidence

ORD record
ord-13835eb569644464b595d1b61a8fc4af
Source dataset
uspto-grants-2008_01
Patent number
US07320986B2

Reaction notes

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