Boron tribromide → HCID 22387344, compound

HRID 1072705Notes

Reaction equation

HRID 1072705 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=3)=[CH:11][C:10]([CH3:21])=[C:9]2[CH3:22])=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9]([CH3:22])=[C:10]([CH3:21])[CH:11]=[C:12]2[C:13]2[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22387513HCID 22387513, compound

Product 1

HCID 22387344HCID 22387344, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(4-bromophenyl)-5-(4-methoxyphenyl)-2,3-dimethyl-1H-pyrrole (610 mg, 1.71 mmol) in methylene chloride (30 ml) was added boron tribromide (0.647 ml, 6.84 mmol) at 0° C. The obtained solution was stirred at 0° C. for 1 hour, poured into ice water and extracted with ethyl acetate. The extracts were collected and washed with saturated aqueous sodium bicarbonate and dried over magnesium sulfate anhydride, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1) to isolate the object compound as an oily substance. 358 mg (yield: 61.2%)

Workup

  1. extractionextracted with ethyl acetate
  2. customThe extracts were collected
  3. washwashed with saturated aqueous sodium bicarbonate
  4. dry with materialdried over magnesium sulfate anhydride
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1)
  7. customto isolate the object compound as an oily substance

Sources & evidence

ORD record
ord-587241978dce4a42af0e720cd58af068
Source dataset
uspto-grants-2005_06
Patent number
US06911468B2

Reaction notes

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