Water → HCID 68654399, compound

HRID 229182Notes

Reaction equation

HRID 229182 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]([Cl: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]([Cl:18])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 43805071HCID 43805071, compound

Product 1

HCID 68654399HCID 68654399, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 70 (2.00 g, 6.14 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 followed by flash chromatography (20:1 to 5:1 hexanes:EtOAc) afforded 1.42 g (74%) of 71. 1H NMR (400 MHz, CDCl3): δ 5.97 (br s, 1H), 6.89 (d, J=8.8 Hz, 2H), 7.23 (d, J=8.1 Hz, 1H), 7.50 (dd, J=8.1 Hz, 1.7 Hz, 1H), 7.64 (d, J=1.7 Hz, 1H), 7.73 (d, J=8.8 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-a868eedc4503431c827c7490dd57db78
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

Loading…