Boron tribromide → HCID 22033137, compound

HRID 1792322Notes

Reaction equation

HRID 1792322 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][S:29][CH2:30][CH2:31][CH2:32][C:33]([F:39])([F:38])[C:34]([F:37])([F:36])[F:35])[C:8]([CH3:19])([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)[CH2:9][O:10]2)=[CH:5][CH:4]=1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][S:29][CH2:30][CH2:31][CH2:32][C:33]([F:39])([F:38])[C:34]([F:37])([F:35])[F:36])[C:8]([CH3:19])([C:13]3[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=3)[CH2:9][O:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 22033203HCID 22033203, compound

Product 1

HCID 22033137HCID 22033137, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3RS,4RS)-7-methoxy-3-methyl-4-[9-(4,4,5,5,5-pentafluoropentylthio)nonyl]-3-(4-pyridyl)chroman (15.2 mg, 0.0265 mmol) in methylene chloride (1 ml) was added at −78° C. BBr3 (1.0 mol/l, 0.080 ml), which was then slowly warmed, and stirred for 2 hours under ice-cooling. After the reaction was completed saturated aqueous NaHCO3, solution was added under ice-cooling, the resulting mixture was then extracted with chloroform and washed with saturated saline solution. The organic layer was dried over magnesium sulfate, and the solvent was removed under reduced pressure. The residue was subjected to silica gel column chromatography (n-hexane:ethyl acetate=1:1) to give (3RS,4RS)-7-hydroxy-3-methyl-4-[9-(4,4,5,5,5-pentafluoropentylthio)nonyl]-3-(4-pyridyl)chroman (6.3 mg, yield 43%).

Workup

  1. temperaturecooling
  2. additionwas added under ice-
  3. temperaturecooling
  4. extractionthe resulting mixture was then extracted with chloroform
  5. washwashed with saturated saline solution
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6b6f15f1e67548649ee2350a6b7d3ce3
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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