Water → HCID 53661303, compound

HRID 229186Notes

Reaction equation

HRID 229186 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16]C)=[CH:12][CH:11]=2)=[O:9])=[C:4]([F:18])[CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-].O>C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[O:9])=[C:4]([F:18])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 11833816HCID 11833816, compound

Product 1

HCID 53661303HCID 53661303, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 75 (1.50 g, 5.08 mmol) and AlCl3 (3.50 g, 26.2 mmol) were refluxed in benzene (50 mL) for 3 h and then cooled to RT. Water (100 mL) was cautiously added dropwise, and the mixture was extracted with Et2O (3×100 mL). The combined ethereal extracts were washed with water (200 mL), brine (200 mL), and dried over MgSO4. Concentration afforded 1.39 g (97%) of 76 that was used without further purification. 1H NMR (400 MHz, CDCl3): δ 5.73 (br s, 1H), 6.90 (d, J=8.8 Hz, 2H), 7.35-7.41 (m, 3H), 7.77 (d, J=8.4 Hz, 2H).

Workup

  1. extractionthe mixture was extracted with Et2O (3×100 mL)
  2. washThe combined ethereal extracts were washed with water (200 mL), brine (200 mL)
  3. dry with materialdried over MgSO4
  4. concentrationConcentration

Sources & evidence

ORD record
ord-e7861210209041918e0d571277568c83
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

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