Water → HCID 22718036, compound

HRID 460452Notes

Reaction equation

HRID 460452 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH:24]([CH2:28][CH2:29][CH2:30][C:31]([F:37])([F:36])[C:32]([F:35])([F:34])[F:33])[C:25]([OH:27])=[O:26])=[C:12]([C:38]1[CH:43]=[CH:42][C:41]([O:44]C)=[CH:40][CH:39]=1)[CH:11]=[CH:10]2.O.C(#N)C>ClCCl>[OH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH:24]([CH2:28][CH2:29][CH2:30][C:31]([F:36])([F:37])[C:32]([F:33])([F:34])[F:35])[C:25]([OH:27])=[O:26])=[C:12]([C:38]1[CH:39]=[CH:40][C:41]([OH:44])=[CH:42][CH:43]=1)[CH:11]=[CH:10]2

Participants

6

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 25134Boron tribromideHCID 22718042HCID 22718042, compound

Product 1

HCID 22718036HCID 22718036, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of boron tribromide in dichloromethane (1.0 M, 8.5 ml, 8.47 mmol) was added dropwise to a solution of 9-[6-methoxy-2-(4-methoxyphenyl)naphth-1-yl]-2-(4,4,5,5,5-pentafluoropentyl)nonanoic acid (820 mg, 1.41 mmol) in dichloromethane (20 ml) at −78° C. under argon atmosphere. The reaction mixture was warmed with stirring to 0° C. over 5 hours. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=3/2), followed by column chromatography on reversed-phase silica gel RP-18 (eluent: acetonitrile containing 0.1% trifluoroacetic acid/water=3/2), to give 9-[6-hydroxy-2-(4-hydroxyphenyl)naphth-1-yl]-2-(4,4,5,5,5-pentafluoropentyl)nonanoic acid (633 mg, Yield 81%).

Workup

  1. temperatureThe reaction mixture was warmed
  2. extractionwas then extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationAfter distilling off the solvent
  6. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=3/2)

Sources & evidence

ORD record
ord-c18c5ea4651a441f9a99d679b44111f7
Source dataset
uspto-grants-2007_03
Patent number
US07196081B2

Reaction notes

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