Boron tribromide → 5-Fluoro-6-hydroxy-1-methanesulphonylindole

HRID 23950

Reaction equation

HRID 23950 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11]C)[N:7]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:6]=[CH:5]2.B(Br)(Br)Br>ClCCl>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[OH:11])[N:7]([S:13]([CH3:16])(=[O:14])=[O:15])[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 225700505-Fluoro-1-methanesulphonyl-6-methoxyindole

Product 1

HCID 225700715-Fluoro-6-hydroxy-1-methanesulphonylindoleYield 74.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-fluoro-1-methanesulphonyl-6-methoxyindole (0.10 g 0.41 mmol) in dry dichloromethane (3 ml) at −10° C. was added a solution of BBr3 (1M in dichloromethane, 1.23 ml) over one minute. The reacture was warmed to room temperature and stirred for 2 h and then poured onto ice/1M hydrochloric acid (10 ml). After stirring for 15 min the mixture was extracted with ethyl acetate (1×50 ml, 2×20 ml), dried (MgSO4) and evaporated in vacuo to give 5-fluoro-6-hydroxy-1-methanesulphonylindole (70 mg)

Workup

  1. additionpoured onto ice/1M hydrochloric acid (10 ml)
  2. stirringAfter stirring for 15 min the mixture
  3. extractionwas extracted with ethyl acetate (1×50 ml, 2×20 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-46e03427e09340a89c5d21712f65d164
Source dataset
uspto-grants-2005_02
Patent number
US06855715B1

Linked notes

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