Dichloromethane → HCID 17980131, compound

HRID 1766248Notes

Reaction equation

HRID 1766248 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:11][Si](C(C)(C)C)(C)C)[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.C(Cl)Cl.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 2724141Tetrabutylammonium FluorideHCID 17980125HCID 17980125, compound

Product 1

HCID 17980131HCID 17980131, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Combine 7-bromo-5-(tert-butyldimethylsilanyloxy)-1H-indole and methylene chloride and treat with tetrabutyl ammonium fluoride (1.0 eq.) at 0° C. After the mixture is stirred for about 1 hour, pour into ethyl acetate, wash with brine, dry the organic layer over Na2SO4 and concentrate. Purify to give 7-bromo-5-hydroxy-1H-indole.

Workup

  1. washwash with brine
  2. dry with materialdry the organic layer over Na2SO4
  3. concentrationconcentrate
  4. customPurify

Sources & evidence

ORD record
ord-4aabc217065740c2bacf3c77be4e2bda
Source dataset
uspto-grants-2007_06
Patent number
US07230011B2

Reaction notes

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