Aluminum bromide → 4-Acetyl-4'-hydroxy-2-nitro biphenyl

HRID 2380150Notes

Reaction equation

HRID 2380150 reaction equation
[Al](Br)(Br)Br.[C:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=2)=[C:10]([N+:22]([O-:24])=[O:23])[CH:9]=1)(=[O:7])[CH3:6].CCCCCC.C(OCC)(=O)C>C1C=CC=CC=1>[C:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=2)=[C:10]([N+:22]([O-:24])=[O:23])[CH:9]=1)(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 24409Aluminum bromideHCID 189566161-(4'-Methoxy-2-nitro-[1,1'-biphenyl]-4-yl)ethanoneHCID 21226206Ethyl acetate hexane

Product 1

HCID 189566144-Acetyl-4'-hydroxy-2-nitro biphenyl

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a stirred solution of AlBr3 (12.6 g, 47.4 mmole) in benzene (45 mL) is added dropwise under nitrogen a solution of the methylether (5 g, 18.45 mmole) of Step A in benzene (12 mL) over 30 minutes. The resulting solution is stirred at room temperature for 3.5 hours. (TLC, 8:2 hexane-ethyl acetate). The mixture is cooled in an ice bath and the complex is decomposed by the dropwise addition of 6N-HC1 (ca. 37 mL). The organic layer is separated and the aqueous phase is reextracted with ether (3x). The combined extracts are concentrated to a small volume and extracted again with 2.5N-NaOH (2×50 mL +1×10 mL). The basic extracts are cooled and acidified with concentrated HCl (to pH 2). The solid is collected and dried (4.27 g, 90% ). It is used in the next step without further purification.

Workup

  1. temperatureThe mixture is cooled in an ice bath
  2. additionthe complex is decomposed by the dropwise addition of 6N-HC1 (ca. 37 mL)
  3. customThe organic layer is separated
  4. concentrationThe combined extracts are concentrated to a small volume
  5. extractionextracted again with 2.5N-NaOH (2×50 mL +1×10 mL)
  6. temperatureThe basic extracts are cooled
  7. customThe solid is collected
  8. customdried (4.27 g, 90% )
  9. customIt is used in the next step without further purification

Sources & evidence

ORD record
ord-c2d31279b37e4f07ad28862e0f2a96d5
Source dataset
uspto-grants-1994_11
Patent number
US05364944

Reaction notes

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