Aluminum bromide → HCID 136337700, compound

HRID 1867531Notes

Reaction equation

HRID 1867531 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]([N:16]([CH3:18])[CH3:17])=[CH:12][C:11]=3[O:19]C)[CH:8]=[CH:9][C:2]=12.[Al](Br)(Br)Br>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]([N:16]([CH3:17])[CH3:18])=[CH:12][C:11]=3[OH:19])[CH:8]=[CH:9][C:2]=12

Participants

4

Reactant 2

HCID 24409Aluminum bromideHCID 68877760HCID 68877760, compound

Product 1

HCID 136337700HCID 136337700, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

140 mg (0.52 mmol) of (4-benzo[1,2,5]oxadiazol-5-yl-3-methoxy-phenyl)-dimethyl-amine are stirred at −10 to 0° C. in 1.7 mL of CH2Cl2, then over 5 minutes treated with 1.7 mL AlBr3 (1.0 M solution in CH2Br2, 3.3 eq.) and stirred another 19 h under warming to rt. Then, the mixture is extracted with brine/ethyl acetate, the combined organic layers dried with sodium sulfate and concentrated. The crude product is column chromatographed with ethyl acetate/hexanes 1:4 to yield after evaporation of the product-containing fractions the desired product as a red solid.

Workup

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

Sources & evidence

ORD record
ord-793af2194b1848c19d429e409c1c7cf5
Source dataset
uspto-grants-2009_12
Patent number
US07632851B2

Reaction notes

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