Boron tribromide → HCID 68556857, compound

HRID 1967577Notes

Reaction equation

HRID 1967577 reaction equation
[CH2:1]([O:3][C:4](=[O:33])[CH2:5][N:6]([C:12]1[CH:17]=[C:16]([Cl:18])[C:15]([O:19][C:20]2[CH:25]=[CH:24][C:23]([O:26]C)=[C:22]([CH:28]([CH2:30][CH3:31])[CH3:29])[CH:21]=2)=[C:14]([Cl:32])[CH:13]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:33])[CH2:5][N:6]([C:12]1[CH:17]=[C:16]([Cl:18])[C:15]([O:19][C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([CH:28]([CH2:30][CH3:31])[CH3:29])[CH:21]=2)=[C:14]([Cl:32])[CH:13]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 24955673HCID 24955673, compound

Product 1

HCID 68556857HCID 68556857, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
22.5 °C

Procedure

A solution of {[4-(3-sec-butyl-4-methoxy-phenoxy)-3,5-dichloro-phenyl]-ethoxycarbonyl-amino}-acetic acid ethyl ester (0.8 g, 1.6 mmol) in CH2Cl2 (16 mL) was cooled to −60° C. under nitrogen atmosphere. To that 1M BBr3 solution (4.8 mL) was added dropwise. The reaction mixture was allowed to warm up to 20-25° C. over 5 h. then diluted with more CH2Cl2 (25 mL) and quenched with H2O. After stirring at 20-25° C. for 30 min, organic phase was separated, washed with H2O, brine & dried over sodium sulphate, filtered and concentrated to give crude product. The crude product was purified by column chromatography over flash silica gel (Hexane:Ethylacetate 90:10) to afford the pure product {[4-(3-sec-Butyl-4-hydroxy-phenoxy)-3,5-dichloro-phenyl]-ethoxycarbonyl-amino}-acetic acid ethyl ester (0.77 g, 99% Yield)

Workup

  1. customquenched with H2O
  2. customorganic phase was separated
  3. washwashed with H2O, brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give crude product
  8. customThe crude product was purified by column chromatography over flash silica gel (Hexane:Ethylacetate 90:10)

Sources & evidence

ORD record
ord-a07a54517784459697e369f6e23b0a93
Source dataset
uspto-grants-2013_04
Patent number
US08420851B2

Reaction notes

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