Bromide ion → Isohexane ethyl acetate

HRID 1823968Notes

Reaction equation

HRID 1823968 reaction equation
[Br-].CC1(C)[C:7]([CH3:9])(C)[O:6]B([C:10]2[CH:11]=[CH:12][C:13]3[CH2:20][C@H]4[C@]5(CN(CC(F)(F)F)S(=O)(=O)N5)[C@H](CC4)C[C:14]=3C=2)O1.[C:35](=[O:38])([O-])[O-].[Na+].[Na+].[C:41]1(C)C=CC=CC=1>C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:35]([O:6][CH2:7][CH3:9])(=[O:38])[CH3:41].[CH3:10][CH2:11][CH2:12][CH:13]([CH3:20])[CH3:14]

Participants

7

Reactant 4

HCID 259Bromide ionHCID 1140TolueneHCID 10340Sodium CarbonateHCID 23571079[6s,9r,11r]2',3',4',5,5',6,7,8,9,10-Decahydro-2-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-5'-(2,2,2-trifluoroethyl)spiro[6,9-methanobenzocyclooctene-11,3'-[1,2,5]thiadiazole]1',1'-dioxide

Product 1

HCID 21882781Isohexane ethyl acetateYield 50%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the bromide from Step 3 (0.075 g), the homochiral boronate ester from Example 24, Step 1 (0.105 g), tetrakis(triphenylphosphine) palladium (0) (0.1 g), 2M aqueous sodium carbonate (0.22 mL) and toluene (3 mL) was refluxed for 4 hours. The mixture was cooled, diluted with ethyl acetate (15 mL) and washed with water (10 ml). The organic phase was filtered through a Teflon membrane and concentrated. Flash column chromatography, eluting with 20% then 30% then 50% ethyl acetate-isohexane, gave the product as a yellow oil (0.085 g, 63%). MS (ES+) 628 ([MH]+).

Workup

  1. temperatureThe mixture was cooled
  2. washwashed with water (10 ml)
  3. filtrationThe organic phase was filtered through a Teflon membrane
  4. concentrationconcentrated
  5. washFlash column chromatography, eluting with 20%

Sources & evidence

ORD record
ord-3cdab137644142c58e92c006fb5139e5
Source dataset
uspto-grants-2006_05
Patent number
US07041689B2

Reaction notes

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