1,3-Dibromopropane → HCID 68471326, compound

HRID 2382673Notes

Reaction equation

HRID 2382673 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:9]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[Br:17][CH2:18][CH2:19][CH2:20]Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:9]=1[O:15][CH2:20][CH2:19][CH2:18][Br:17])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 19040054tert-Butyl (2-hydroxy-6-methylphenyl)carbamate

Product 1

HCID 68471326HCID 68471326, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
55 °C

Procedure

To (2-hydroxy-6-methyl-phenyl)-carbamic acid tert-butyl ester (5.5 g, 24.6 mmol) in acetonitrile (200 mL) was added 1,3-dibromopropane (17.5 mL, 172 mmol), and potassium carbonate (27.0 g, 196 mmol). The mixture was heated at 55° C. for 2.5 hrs, followed by a filtration to remove solids. The filtrate was concentrated and repartitioned with ethyl acetate (250 mL) and water (150 mL). The organic layer was then washed with brine (150 mL), dried over MgSO4, and evaporated affording [2-(3-bromo-propoxy)-6-methyl-phenyl]-carbamic acid tert-butyl ester (quantitative yield). MS: 243.8 (M+H-Boc)+; tR=2.62 min (method 1).

Workup

  1. filtrationfollowed by a filtration
  2. customto remove solids
  3. concentrationThe filtrate was concentrated
  4. washThe organic layer was then washed with brine (150 mL)
  5. dry with materialdried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-507a039ccb7e43ee9a39f73969130c9c
Source dataset
uspto-grants-2012_09
Patent number
US08263588B2

Reaction notes

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