Ammonium Chloride → HCID 17980125, compound

HRID 1766247Notes

Reaction equation

HRID 1766247 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.[CH:19]([Mg]Br)=[CH2:20].[NH4+].[Cl-]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH:5]=[C:6]2[C:7]=1[NH:8][CH:20]=[CH:19]2

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 17980115HCID 17980115, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 17980125HCID 17980125, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-45 °C

Procedure

Combine 3-bromo-4-nitro-1-tert-butyldimethylsilyloxybenzene and dry THF. Cool to about −45° C. and then treat with vinylmagnesium bromide (1.2 eq.) over a few minutes. After about 45 minutes, pour the reaction mixture into saturated aq. NH4Cl, extract with ether, combined the organic extracts and extract with water, dry over Na2SO4 and concentrate. Purify to give 7-bromo-5-(tert-butyldimethylsilanyloxy)-1H-indole.

Workup

  1. extractionextract with ether
  2. extractionextract with water
  3. dry with materialdry over Na2SO4
  4. concentrationconcentrate
  5. customPurify

Sources & evidence

ORD record
ord-9fd35fda23cc4dc8a20c71467890914b
Source dataset
uspto-grants-2007_06
Patent number
US07230011B2

Reaction notes

Loading…