Boron tribromide → HCID 22030883, compound

HRID 1791768Notes

Reaction equation

HRID 1791768 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([CH3:11])[NH:8]2)=[CH:4][C:3]=1[O:12]C.B(Br)(Br)Br>C(Cl)Cl>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([CH3:11])[NH:8]2)=[CH:4][C:3]=1[OH:12]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22030545HCID 22030545, compound

Product 1

HCID 22030883HCID 22030883, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-30 °C

Procedure

To a solution of 6-fluoro-5-methoxy-2-methylindole (1.23 g, 6.86 mmol), (prepared as described for the starting material in Example 237), in methylene chloride (15 ml) cooled at −30° C. was added a solution of boron tribromide (3.78 g, 15.1 mmol) in methylene chloride (2 ml). After stirring for 90 minutes at ambient temperature, the mixture was poured onto ice and diluted with methylene chloride. The pH of the aqueous layer was adjusted to 6. The organic layer was separated, washed with water, brine, dried (MgSO4) and evaporated. The residue was purified by column chromatography eluting with ethylacetate/petroleum ether (8/2) to give 6-fluoro-5-hydroxy-2-methylindole (905 mg, 80%).

Workup

  1. additionthe mixture was poured onto ice
  2. customThe organic layer was separated
  3. washwashed with water, brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by column chromatography
  7. washeluting with ethylacetate/petroleum ether (8/2)

Sources & evidence

ORD record
ord-a44682b619e34067b2df51e2ad64decc
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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