Benzyl Bromide → HCID 15851500, compound

HRID 2394370Notes

Reaction equation

HRID 2394370 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].[OH-].[Na+].[CH2:9](Br)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>O1CCCC1>[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][O:4][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 118072-Amino-2-methyl-1-propanolHCID 14798Sodium Hydroxide

Product 1

HCID 15851500HCID 15851500, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-amino-2-methyl-1-propanol (7.1 mmol) in tetrahydrofuran (THF) (25 mL) was added dropwise to a slurry of 60% sodium hydroxide/oil (3 g, 75 mmol) in THF (75 mL). The mixture was stirred at room temperature for 1 hour and then cooled in an ice bath. A solution of benzyl bromide (5.9 mL, 50 mmol) was added dropwise. After stirring for 2 hours at 0° C., the reaction mixture was poured into ice/water and extracted with ethyl acetate. The organic phase was washed with brine, dried (MgSO4) and concentrated to an oil which was subjected to flash chromatography on silica gel eluting with 5% methanol/chloroform. Fractions containing the desired product were combined and concentrated to yield an oil. Yield: 4.2 g (47%).

Workup

  1. temperaturecooled in an ice bath
  2. stirringAfter stirring for 2 hours at 0° C.
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated to an oil which
  7. additionFractions containing the desired product
  8. concentrationconcentrated
  9. customto yield an oil

Sources & evidence

ORD record
ord-360f71596df14609abc1b0cba215d552
Source dataset
uspto-grants-1998_09
Patent number
US05811432

Reaction notes

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