Hydrochloric Acid → HCID 68654435, compound

HRID 229264Notes

Reaction equation

HRID 229264 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16]C)[CH:11]=2)=[O:9])=[CH:4][C:3]=1[F:18].[Al+3].[Cl-].[Cl-].[Cl-].Cl>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[CH:11]=2)=[O:9])=[CH:4][C:3]=1[F:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 24722787(4-Bromo-3-fluorophenyl)(3-methoxyphenyl)methanone

Product 1

HCID 68654435HCID 68654435, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The demethylation procedure described for 2 was employed. To a stirred solution of (4-bromo-3-fluorophenyl)[3-(methyloxy)phenyl]methanone (1.0 g, 2.5 mol) in toluene (50 mL) was slowly added AlCl3 (1.3 g, 9.7 mol) via a powder addition funnel under a nitrogen atmosphere at room temperature. The stirred reaction mixture was heated at reflux for 3 h. The reaction mixture was allowed to cool to room temperature and then poured into 10% aqueous HCl (200 mL). Standard work-up yielded 0.935 g (100%) of the title compound 196 as a tan solid. 1H NMR (300 MHz, CDCl3): δ 7.71 and 7.68 (dd, J1=6.6 Hz, J2=6.6 Hz, 1H), 7.60 and 7.57 (dd, J1=8.7 Hz, J2=1.5 Hz, 1H), 7.50 and 7.47 (dd, J1=8.1 Hz, J2=1.2 Hz, 1H), 7.41-7.31 (m 3H), 7.15 and 7.13 (dd, J1=7.8 Hz, J2=1.8 Hz, 1H), 5.93(s, 1H).

Workup

  1. additionvia a powder addition funnel under a nitrogen atmosphere at room temperature
  2. customThe stirred reaction mixture
  3. temperaturewas heated
  4. temperatureat reflux for 3 h

Sources & evidence

ORD record
ord-021aecc3247c462c8118c45c6c8e901d
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

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