Water → HCID 58437402, compound

HRID 73375Notes

Reaction equation

HRID 73375 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([O:21]CC4C=CC=CC=4)=[C:17]([Cl:20])[CH:18]=3)[C:13]([C:29]#[N:30])=[CH:12]2)=[CH:7][CH:6]=1)[CH3:2].B(Br)(Br)Br.O>ClCCl>[CH2:1]([O:3][C:4](=[O:31])[C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([OH:21])=[C:17]([Cl:20])[CH:18]=3)[C:13]([C:29]#[N:30])=[CH:12]2)=[CH:9][CH:10]=1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 58437227HCID 58437227, compound

Product 1

HCID 58437402HCID 58437402, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(5-benzyloxy-6-chloro-3-cyanoindol-1-yl)benzoic acid ethyl ester (0.310 g) in dichloromethane (7 mL) was added boron tribromide (1 mol/L dichloromethane solution) (0.860 mL) under ice cooling, and this mixture was stirred at the same temperature for 1 hour. To this reaction mixture was added water, this mixture was extracted with ethyl acetate. This organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. This filtrate was removed under reduced pressure. The residue was washed with diethyl ether to give the title compound (0.181 g).

Workup

  1. extractionthis mixture was extracted with ethyl acetate
  2. washThis organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThis filtrate was removed under reduced pressure
  6. washThe residue was washed with diethyl ether

Sources & evidence

ORD record
ord-28f96f15e1c244fb9e0a81bc1dcebf99
Source dataset
uspto-grants-2014_09
Patent number
US08829040B2

Reaction notes

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