Sulfuric acid magnesium salt (1:1) → HCID 178521076, compound

HRID 1930504Notes

Reaction equation

HRID 1930504 reaction equation
[NH2:1][C@@H:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][OH:4].[Br:11][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH:14]=O.S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)Cl.CCOCC>[Br:11][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1/[CH:14]=[N:1]/[C@@H:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][OH:4]

Participants

6

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 811292-BromobenzaldehydeHCID 1347972-Amino-2-phenylethan-1-ol

Product 1

HCID 178521076HCID 178521076, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (S)-(+)-2-amino-2-phenylethanol (271 mmol, 37.2 g) in methylene chloride (350 mL) was added 2-bromobenzaldehyde (271 mmol, 31.8 mL, 50.2 g) and anhydrous magnesium sulfate (50 g). The mixture stirred 3 h at room temperature then left to stand overnight. Filtered through dicalite and evaporated to dryness to give a pale yellow solid. This solid was stirred in dry ether (100 mL) for 30 min, then filtered, washed with ether, and dried in vacuo to give (S,E)-2-(2-bromobenzylideneamino)-2-phenylethanol (65.1 g) as a colourless solid.

Workup

  1. waitthen left
  2. waitto stand overnight
  3. filtrationFiltered through dicalite
  4. customevaporated to dryness
  5. customto give a pale yellow solid
  6. filtrationfiltered
  7. washwashed with ether
  8. customdried in vacuo

Sources & evidence

ORD record
ord-226e85fc3cd44d8a8901ae36c8f0e060
Source dataset
uspto-grants-2012_05
Patent number
US08188123B2

Reaction notes

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