1-Benzyloxy-4-bromo-2-fluoro-5-nitrobenzene → 4-(benzyloxy)-7-bromo-5-fluoro-1H-indole

HRID 2421229Notes

Reaction equation

HRID 2421229 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][C:3]=1[N+:17]([O-])=O.[CH:20]([Mg]Br)=[CH2:21]>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:4]2[C:3]=1[NH:17][CH:21]=[CH:20]2

Participants

4

Reactant 2

HCID 583039441-Benzyloxy-4-bromo-2-fluoro-5-nitrobenzeneHCID 178418507HCID 178418507, compound

Product 1

HCID 583038564-(benzyloxy)-7-bromo-5-fluoro-1H-indoleYield 34.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

A solution of 1-bromo-5-fluoro-2-nitro-4-[(phenylmethyl)oxy]benzene (D4) (10.58 g, 32.4 mmol) in THF was cooled to −40° C. under argon and vinylmagnesium bromide (97 mL of 1M solution in THF, 97 mmol) was added quickly via syringe. The temperature reached ˜−30° C. before cooling down to −40° C. The mixture was stirred at −40° C. for 40 mins and then quenched by the addition of NH4Cl solution. The mixture was allowed to reach room temperature and the layers were separated. The aqueous layer was reextracted with ethyl acetate and the combined organic layers were dried (Na2SO4) and evaporated. Chromatography on silica gel (elution with 0-50% ethyl acetate in hexane) gave the title compound as an orange oil (D5), (3.6 g).

Workup

  1. customreached ˜−30° C.
  2. customquenched by the addition of NH4Cl solution
  3. customto reach room temperature
  4. customthe layers were separated
  5. dry with materialthe combined organic layers were dried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-c9b235a31db94f6b9a4dbfcf0deb848d
Source dataset
uspto-grants-2011_06
Patent number
US07956083B2

Reaction notes

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