Boron tribromide → 2-hydroxy-N,N,2-tri(4-hydroxyphenyl)propanamide

HRID 476346Notes

Reaction equation

HRID 476346 reaction equation
[OH:1][C:2]([C:23]1[CH:28]=[CH:27][C:26]([O:29]C)=[CH:25][CH:24]=1)([CH3:22])[C:3]([N:5]([C:14]1[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=1)[C:6]1[CH:11]=[CH:10][C:9]([O:12]C)=[CH:8][CH:7]=1)=[O:4].B(Br)(Br)Br>C(Cl)Cl>[OH:1][C:2]([C:23]1[CH:24]=[CH:25][C:26]([OH:29])=[CH:27][CH:28]=1)([CH3:22])[C:3]([N:5]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)=[O:4]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 576081272-hydroxy-N,N,2-tris(4-methoxyphenyl)propanamide

Product 1

HCID 235823882-hydroxy-N,N,2-tri(4-hydroxyphenyl)propanamideYield 77.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-hydroxy-N,N,2-tris(4-methoxyphenyl)propanamide (0.60 g, 1.47 mmol) was to dissolved in 30 mL of anhydrous methylene chloride in a dry 250 mL round-bottomed flask fitted with a stiffing bar, anitrogen inlet and rubber stopper. BBr3 solution (6.00 mL of 1M CH2Cl2 solution, 6.00 mmol) was added dropwise with stiffing at 0° C. The reaction solution was stirred at room temperature overnight. The reaction was quenched by adding 20 mL of water and extracted with EtOAc (3×30 mL). The EtOAc layers were separated and dried over anhydrous MgSO4. The solvent was removed under reduced pressure. The residue was purified by flash column chromatography (silica gel, CH2Cl2/MeOH=9/1 v/v) to give a white solid product, 2-hydroxy-N,N,2-tri(4-hydroxyphenyl)propanamide (11k), 0.42 g, 77.8% yield.

Workup

  1. customfitted with a stiffing bar, anitrogen inlet
  2. customwith stiffing at 0° C
  3. customThe reaction was quenched
  4. additionby adding 20 mL of water
  5. extractionextracted with EtOAc (3×30 mL)
  6. customThe EtOAc layers were separated
  7. dry with materialdried over anhydrous MgSO4
  8. customThe solvent was removed under reduced pressure
  9. customThe residue was purified by flash column chromatography (silica gel, CH2Cl2/MeOH=9/1 v/v)

Sources & evidence

ORD record
ord-4fb52506f8bc4413b03a63cb93c8f824
Source dataset
uspto-grants-2014_01
Patent number
US08637706B2

Reaction notes

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