Allyl bromide → HCID 57655922, compound

HRID 2041125Notes

Reaction equation

HRID 2041125 reaction equation
[OH:1][C:2]1[C:12]2[CH2:11][CH2:10][N:9]([C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])[CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:25](Br)[CH:26]=[CH2:27]>CC(C)=O>[CH2:27]([O:1][C:2]1[C:12]2[CH2:11][CH2:10][N:9]([C:13](=[O:18])[C:14]([F:17])([F:15])[F:16])[CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)[CH:26]=[CH2:25]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 22219609HCID 22219609, compound

Product 1

HCID 57655922HCID 57655922, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Dissolve 6-hydroxy-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (1 g, 3.9 mmol) in acetone (5 mL) and add powdered potassium carbonate (2.8 g, 20 mmol). Add dropwise a solution of allyl bromide (1.04 mL, 12 mmol) in acetone (3 mL) over 10 min and stir at ambient temperature overnight. Filter solids, wash with acetone and concentrate in vacuo to give the desired intermediate as an off-white solid (1.15 g, 98%). GC-MS m/z: 299 (M+).

Workup

  1. filtrationFilter solids
  2. washwash with acetone
  3. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-d62c20e055064e4a83febf069e5afb8e
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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