Methanol → HCID 73213469, compound

HRID 1773077Notes

Reaction equation

HRID 1773077 reaction equation
[C:1]12([C:11]3[C:12]([OH:32])=[CH:13][C:14]([OH:31])=[C:15]([CH:30]=3)[C:16]([NH:18][CH2:19][C:20]3[CH:25]=[C:24]([O:26]C)[CH:23]=[CH:22][C:21]=3[O:28]C)=[O:17])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.B(Br)(Br)Br.CO>ClCCl>[C:1]12([C:11]3[C:12]([OH:32])=[CH:13][C:14]([OH:31])=[C:15]([CH:30]=3)[C:16]([NH:18][CH2:19][C:20]3[CH:25]=[C:24]([OH:26])[CH:23]=[CH:22][C:21]=3[OH:28])=[O:17])[CH2:10][CH:5]3[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]3)[CH2:8]1)[CH2:2]2

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 73213468HCID 73213468, compound

Product 1

HCID 73213469HCID 73213469, compoundYield 7.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Adamantan-1-yl-N-(2,5-dimethoxybenzyl)-2,4-dihydroxybenzamide (0.27 g) is dissolved in dichloromethane (3 mL). After adding BBr3 (1.7 mL in CH2Cl2 1.0 M solution, 3 eq.) and stirring at room temperature for 2 hours, methanol (5 mL) is added and extraction is carried out using water and dichloromethane. The organic layer is dried with anhydrous magnesium sulfate, filtered, concentrated under reduced pressure and separated by column chromatography to obtain 0.02 g of the target compound as white solid.

Workup

  1. extractionextraction
  2. dry with materialThe organic layer is dried with anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customseparated by column chromatography

Sources & evidence

ORD record
ord-d2cb5fc45a0046f19bfda2fcb3b692cb
Source dataset
uspto-grants-2016_02
Patent number
US09254251B2

Reaction notes

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