Methanol → HCID 86729946, compound

HRID 1773078Notes

Reaction equation

HRID 1773078 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][CH3:27])[CH:23]=[C:22]([O:28]C)[CH:21]=3)=[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]([O:26][CH3:27])[CH:23]=[C:22]([OH:28])[CH:21]=3)=[O:17])[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 73212612HCID 73212612, compound

Product 1

HCID 86729946HCID 86729946, compoundYield 17.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Adamantan-1-yl-N-(3,5-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 0.045 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-fba2ef50fc0b430199a063375b7f5e38
Source dataset
uspto-grants-2016_02
Patent number
US09254251B2

Reaction notes

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