Boron tribromide → HCID 68554902, compound

HRID 1967581Notes

Reaction equation

HRID 1967581 reaction equation
C([O:3][C:4](=[O:34])[CH2:5][N:6]([C:13]1[CH:18]=[C:17]([Cl:19])[C:16]([O:20][C:21]2[CH:26]=[CH:25][C:24]([O:27]C)=[C:23]([CH:29]([CH2:31][CH3:32])[CH3:30])[CH:22]=2)=[C:15]([Cl:33])[CH:14]=1)[CH2:7][C:8]([O:10]CC)=[O:9])C.B(Br)(Br)Br>C(Cl)Cl>[CH:29]([C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][C:24]=1[OH:27])[O:20][C:16]1[C:15]([Cl:33])=[CH:14][C:13]([N:6]([CH2:7][C:8]([OH:10])=[O:9])[CH2:5][C:4]([OH:34])=[O:3])=[CH:18][C:17]=1[Cl:19])([CH2:31][CH3:32])[CH3:30]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68554790HCID 68554790, compound

Product 1

HCID 68554902HCID 68554902, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
22.5 °C

Procedure

To a solution of {[4-(3-sec-Butyl-4-methoxy-phenoxy)-3,5-dichloro-phenyl]-ethoxycarbonylmethyl-amino}-acetic acid ethyl ester (12.5 g, 0.02 mol) in CH2Cl2 (250 mL) was cooled to −60° C. under nitrogen atmosphere. To that 1M BBr3 solution (122 mL) was added dropwise. The reaction mixture was allowed to warm up to 20-25° C. over 5 h. then diluted with more CH2Cl2 (250 mL) and quenched with H2O. After stirring at 20-25° C. for 30 min, organic phase was separated, washed with water, brine, dried over sodium sulphate, filtered and concentrated to give crude product. The crude product was purified by column chromatography over flash silica gel (chloroform:methanol) gradient elution from 95:5 to 90:10 to give pure {[4-(3-sec-Butyl-4-hydroxy-phenoxy)-3,5-dichloro-phenyl]-carboxymethyl-amino}-acetic acid (6.8 g, 63% yield)

Workup

  1. customquenched with H2O
  2. customorganic phase was separated
  3. washwashed with water, 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 (chloroform:methanol) gradient elution from 95:5 to 90:10

Sources & evidence

ORD record
ord-fc027895435542718b03f00234ef0dab
Source dataset
uspto-grants-2013_04
Patent number
US08420851B2

Reaction notes

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