Boron tribromide → HCID 10715977, compound

HRID 37726Notes

Reaction equation

HRID 37726 reaction equation
[C:1]([C:4]1[C:5]([CH3:31])=[C:6]([C@@H:14]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22]C)=[O:21])[C:7]([O:12]C)=[C:8]([CH3:11])[C:9]=1[CH3:10])(=[O:3])[CH3:2].B(Br)(Br)Br>ClCCl>[C:1]([C:4]1[C:5]([CH3:31])=[C:6]([C@@H:14]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[C:7]([OH:12])=[C:8]([CH3:11])[C:9]=1[CH3:10])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 10812460methyl (R)-7-(3-acetyl-6-methoxy-2,4,5-trimethylphenyl)-7-(4-fluorophenyl)heptanoate

Product 1

HCID 10715977HCID 10715977, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methyl (R)-7-(3-acetyl-6-methoxy-2,4,5-trimethylphenyl)-7-(4-fluorophenyl)heptanoate (2.0 g, 4.7 mmol) in dichloromethane (10 ml) was added dropwise to boron tribromide (2.0 ml, 5.3 g, 21.0 mmol) in dichloromethane (30 ml) at -78° C. The temperature of the reaction solution was elevated gradually to room temperature, and the reaction solution was stirred for 6 hours at the same temperature. To the reaction solution was was added ice-water at 0° C., and the mixture was extracted with ethyl acetate. The organic layer was washed with water, a saturated aqueous solution of sodium chloride in the order mentioned, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was subjected to a silica gel column chromatography to give (R)-7-(3-acetyl-6-hydroxy-2,4,5-trimethylphenyl)-7-(4-fluorophenyl)heptanoic acid (1.56 g). Physico-chemical properties and spectral data are shown in [Table 5].

Workup

  1. customwas elevated gradually to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-ca138925fce14f1aacf12f939a9cf3c1
Source dataset
uspto-grants-1995_05
Patent number
US05420363

Reaction notes

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