Aluminum bromide → HCID 136337695, compound

HRID 1867528Notes

Reaction equation

HRID 1867528 reaction equation
[N:1]1[O:5][N:4]=[C:3]2[CH:6]=[C:7]([C:10]3[CH:15]=[CH:14][C:13]([NH:16][CH3:17])=[CH:12][C:11]=3[O:18]C)[CH:8]=[CH:9][C:2]=12.[Al](Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[N:1]1[O:5][N:4]=[C:3]2[CH:6]=[C:7]([C:10]3[CH:15]=[CH:14][C:13]([NH:16][CH3:17])=[CH:12][C:11]=3[OH:18])[CH:8]=[CH:9][C:2]=12

Participants

5

Reactant 3

HCID 24409Aluminum bromideHCID 516892Sodium BicarbonateHCID 68878052HCID 68878052, compound

Product 1

HCID 136337695HCID 136337695, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

100 mg (0.4 mmol) of (4-benzo[1,2,5]oxadiazol-5-yl-3-methoxy-phenyl)-methyl-amine are stirred at −10 to 0° C. in 1.3 mL of CH2Cl2, then over 5 minutes treated with 1.3 mL AlBr3 (1.0 M solution in CH2Br2, 3 eq.) and stirred another 17 h under warming to rt. Then, the mixture is poured onto brine/ethyl acetate and the pH adjusted to 6 using NaHCO3. Then the aqueous phase is extracted with ethyl acetate, the combined organic layers dried with sodium sulfate and concentrated. The crude product is column chromatographed with ethyl acetate/hexanes 1:1 to yield after evaporation of the product-containing fractions the desired product as a yellow solid.

Workup

  1. additionThen, the mixture is poured onto brine/ethyl acetate
  2. extractionThen the aqueous phase is extracted with ethyl acetate
  3. dry with materialthe combined organic layers dried with sodium sulfate
  4. concentrationconcentrated
  5. customchromatographed with ethyl acetate/hexanes 1:1
  6. customto yield
  7. customafter evaporation of the product-containing fractions the desired product as a yellow solid

Sources & evidence

ORD record
ord-350680f30aab491896f2f0aa40509d3a
Source dataset
uspto-grants-2009_12
Patent number
US07632851B2

Reaction notes

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