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

HRID 1694780Notes

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

Conditions

Temperature: 0 °C

Procedure

2-hydroxy-N,N,2-tris(4-methoxyphenyl)propanamide (0.60 g, 1.47 mmol) was dissolved in 30 mL of anhydrous methylene chloride in a dry 250 mL round-bottomed flask fitted with a stirring bar, anitrogen inlet and rubber stopper. BBr3 solution (6.00 mL of 1 M CH2Cl2 solution, 6.00 mmol) was added dropwise with stirring 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

customfitted with a stirring bar, anitrogen inlet
stirringThe reaction solution was stirred at room temperature overnight
customThe reaction was quenched
additionby adding 20 mL of water
extractionextracted with EtOAc (3×30 mL)
customThe EtOAc layers were separated
dry with materialdried over anhydrous MgSO4
customThe solvent was removed under reduced pressure
customThe residue was purified by flash column chromatography (silica gel, CH2Cl2/MeOH=9/1 v/v)

Sources & evidence

ORD record: ord-f187ca7670f6449abd91ecc381f4f3ea
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158828B2

Reaction notes

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