Hydrogen Bromide → 1-[(1R,2R)-3-bromo-1-ethyl-2-methylpropyl]-3-(phenylmethoxy)benzene

HRID 1771020Notes

Reaction equation

HRID 1771020 reaction equation
[CH2:1]([C@@H:3]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:9]=1)[C@@H:4]([CH3:7])[CH2:5]O)[CH3:2].[BrH:22].O>ClCCl>[Br:22][CH2:5][C@H:4]([CH3:7])[C@H:3]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:9]=1)[CH2:1][CH3:2]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 60164839(betaR,gammaR)-gamma-ethyl-beta-methyl-3-(phenylmethoxy)benzenepropanol

Product 1

HCID 601648441-[(1R,2R)-3-bromo-1-ethyl-2-methylpropyl]-3-(phenylmethoxy)benzeneYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of Example 32 (2.6 g, 9 mmol) was dissolved in dichloromethane, and the mixture was cooled in an ice-water bath, then 48% hydrobromic acid (0.54 mL, 10 mmol) was added dropwise, after the addition was complete, it was reacted at room temperature for 16 hours. After that, water was added therein for separating, the aqueous phase was extracted with dichloromethane three times, then the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated to give the target compound 2.7 g, yield: 87%.

Workup

  1. temperaturethe mixture was cooled in an ice-water bath
  2. additionafter the addition
  3. customit was reacted at room temperature for 16 hours
  4. customfor separating
  5. extractionthe aqueous phase was extracted with dichloromethane three times
  6. washwashed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f4751db056184ce698d8830437082d0b
Source dataset
uspto-grants-2016_02
Patent number
US09249084B2

Reaction notes

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