Sodium Iodide → HCID 57608436, compound

HRID 454377Notes

Reaction equation

HRID 454377 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH:9]([OH:12])[CH2:10]Cl)[CH:5]=[CH:6][CH:7]=1.[N-:13]=[N+:14]=[N-:15].[Na+].[Na+].[I-]>CN(C=O)C.CCOCC>[N:13]([CH2:10][CH:9]([OH:12])[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)=[N+:14]=[N-:15]

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 33557Sodium AzideHCID 576084881-(3-Bromophenyl)-3-chloropropan-2-ol

Product 1

HCID 57608436HCID 57608436, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 1-(3-bromophenyl)-3-chloropropan-2-ol (8.49 g, 34.0 mmol) in anhydrous DMF (100 mL) under N2 was added NaN3 (11.05 g, 170.0 mmol) and NaI (cat., 0.75 g, 5.0 mmol). The mixture was heated at 75° C. overnight. After cooling to room temperature, the mixture was diluted with ether and washed with water and brine. The solution was dried over Na2SO4 and concentrated under reduced pressure. The product was dried in a vacuum oven at 40° C. for 2 h to give 1-azido-3-(3-bromophenyl)propan-2-ol as a yellow oil which was used without purification. Yield (8.6 g, 98% crude).

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water and brine
  3. dry with materialThe solution was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe product was dried in a vacuum oven at 40° C. for 2 h

Sources & evidence

ORD record
ord-748d139ad08847939574e99e5b020eea
Source dataset
uspto-grants-2013_07
Patent number
US08492589B2

Reaction notes

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