Boron tribromide → HCID 22030883, compound

HRID 454246Notes

Reaction equation

HRID 454246 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-7448bf404feb449db4ad1f0744030c5b
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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