1,3-Dibromopropane → HCID 71114427, compound

HRID 331034Notes

Reaction equation

HRID 331034 reaction equation
[Br:1][C:2]1[C:3]([OH:16])=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[CH:6][CH:7]=1.Br[CH2:18][CH2:19][CH2:20]Br.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Br:1][C:2]1[C:3]2[O:16][CH2:18][CH2:19][CH2:20][N:8]([C:9]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:15])[C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 71114555HCID 71114555, compound

Product 1

HCID 71114427HCID 71114427, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of tert-butyl (3-bromo-2-hydroxyphenyl)carbamate (D52) (3 g, 10.41 mmol) in acetone (30 mL) was added 1,3-dibromopropane (3.17 mL, 31.2 mmol), K2CO3 (11.51 g, 83 mmol) and the mixture stirred at 75° C. for 16 hours. The reaction was then cooled to RT, filtered, the filtrate was evaporated. The residue was then purified on silica eluting with a gradient of 0-10% ethyl acetate in cyclohexane to afford the title compound (2.2 g). LCMS (A): m/z (M+H)+328/330, C14H18BrNO3 requires 327/329 (acidic).

Workup

  1. temperatureThe reaction was then cooled to RT
  2. filtrationfiltered
  3. customthe filtrate was evaporated
  4. customThe residue was then purified on silica eluting with a gradient of 0-10% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-66d99be8466f4d4eb9f78a90cf7a218f
Source dataset
uspto-grants-2014_11
Patent number
US08877742B2

Reaction notes

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