Boron tribromide → HCID 23114351, compound

HRID 2376399Notes

Reaction equation

HRID 2376399 reaction equation
[CH:1]([C:4]1[CH:28]=[CH:27][C:7]([CH2:8][C:9]2[C:10]([CH3:26])=[C:11]([NH:18][C:19](=[O:25])[CH2:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C:12]([CH3:17])=[CH:13][C:14]=2[O:15]C)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].B(Br)(Br)Br.C(=O)([O-])O.[Na+]>ClCCl>[CH:1]([C:4]1[CH:28]=[CH:27][C:7]([CH2:8][C:9]2[C:10]([CH3:26])=[C:11]([NH:18][C:19](=[O:25])[CH2:20][C:21]([CH3:22])([CH3:24])[CH3:23])[C:12]([CH3:17])=[CH:13][C:14]=2[OH:15])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 23114264HCID 23114264, compound

Product 1

HCID 23114351HCID 23114351, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-(3-(4-isopropylbenzyl)-4-methoxy-2,6-dimethylphenyl)-3,3-dimethylbutanamide obtained in Reference Example 333 (1.99 g, 5.21 mmol) in dichloromethane (25 mL) was added dropwise boron tribromide (a 1.0 M dichloromethane solution, 10.4 mL, 10.4 mmol) under argon atmosphere at −78° C., and the mixture was stirred for 30 minutes. The reaction solution was warmed to room temperature and was stirred for 14 hours. The reaction solution was added to a saturated sodium hydrogen carbonate solution to separate the organic layer, and then the aqueous layer was extracted with ethyl acetate. The entire organic layer was washed with a saturated brine, dried over anhydrous sodium sulfate, filtered and then concentrated under reduced pressure to obtain 1.83 g (yield 97%) of the oily title compound. Melting point: 202-203° C. (ethyl acetate).

Workup

  1. stirringwas stirred for 14 hours
  2. customto separate the organic layer
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe entire organic layer was washed with a saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c697582b21cf46ccaab432dcddcd55f8
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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