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

HRID 2377245Notes

Reaction equation

HRID 2377245 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>ClCCl>[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-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5,6-dimethoxy-indan-1-one (6.1 g, 31.7 mmol) in dichloromethane (150 mL) was cooled to about −78° C. and boron tribromide (7.1 mL, 75.1 mmol) was added dropwise. After the addition, the reaction was stirred for about 1 hour while being allowed to warm to room temperature. The mixture was poured into ice water under vigorous stirring. The pink precipitate was collected by filtration, washed with water, and dried under high vacuum to provide the desired product. MS (APCI): m/z 165 (M+H)+.

Workup

  1. additionAfter the addition
  2. filtrationThe pink precipitate was collected by filtration
  3. washwashed with water
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-07a5328fb61f4a19a2dfd9562fb8060d
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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