Boron tribromide → HCID 54549095, compound

HRID 443049Notes

Reaction equation

HRID 443049 reaction equation
[C:1]([C:3]([C:22]1[CH:27]=[CH:26][C:25]([O:28]C)=[CH:24][CH:23]=1)([C:14]1[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])#[N:2].B(Br)(Br)Br>ClCCl>[C:1]([C:3]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)([C:22]1[CH:23]=[CH:24][C:25]([OH:28])=[CH:26][CH:27]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])#[N:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 54232873HCID 54232873, compound

Product 1

HCID 54549095HCID 54549095, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-70 °C

Procedure

To a solution of ethyl 7-cyano-7,7-bis(4-methoxyphenyl)heptanoate (2.0 g, 5 mmol.) in dichloromethane (20 ml) was added dropwise a solution of boron tribromide (5.07 g, 20 mmol.) in dichloromethane (15 ml) while stirring at -70° C. The reaction mixture was warmed up to 5° C. taking 2 hours, to which was added ice-water, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was subjected to a silica gel column chromatography, eluting with hexane--ethyl acetate (2:1), to afford the title compound (1.7 g).

Workup

  1. temperatureThe reaction mixture was warmed up to 5° C.
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous saline solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. washeluting with hexane--ethyl acetate (2:1)

Sources & evidence

ORD record
ord-4181bf2ee9d344008588203a2b7180ce
Source dataset
uspto-grants-1999_04
Patent number
US05891916

Reaction notes

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