Potassium Carbonate → HCID 68276125, compound

HRID 1400315Notes

Reaction equation

HRID 1400315 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([Cl:12])=[C:7]([OH:13])[CH:6]=[CH:5]2.C([O-])([O-])=O.[K+].[K+].Br[CH2:21][CH2:22][NH:23]C(=O)OC(C)(C)C.CCCCCC.C(OCC)(=O)C>C(#N)C>[Cl-:12].[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([Cl:12])=[C:7]([O:13][CH2:21][CH2:22][NH3+:23])[CH:6]=[CH:5]2

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 21226206Ethyl acetate hexaneHCID 220481596-Bromo-1-chloronaphthalen-2-ol2×

Product 1

HCID 68276125HCID 68276125, compoundYield 138.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 6-bromo-1-chloronaphthalen-2-ol (100 mg, 0.39 mmol) and K2CO3 (108 mg, 0.78 mmol) in 4 mL of acetonitrile was added tert-butyl (2-bromoethyl)carbamate (175 mg, 0.78 mmol). The resulting mixture was heated at 60° C. for 2 h. After TLC control (n-hexane/ethyl acetate 90:10) showed the disappearance of 6-bromo-1-chloronaphthalen-2-ol, solvent was evaporated in vacuo and the crude was taken up in 10 mL of 4M HCl in dioxane and stirred for 1 h. The solvent was removed under vacuum and the residue was diluted with n-hexane (10 mL) and triturated at room temperature overnight. The solid was filtered and dried under vacuum at 50° C. to afford 2-[(6-bromo-1-chloronaphthalen-2-yl)oxy]ethanaminium chloride as white solid (91 mg, 69% yield). HPLC-MS (ESI+): m/z 337.83 [M+H+].

Workup

  1. customwas evaporated in vacuo
  2. customThe solvent was removed under vacuum
  3. additionthe residue was diluted with n-hexane (10 mL)
  4. customtriturated at room temperature overnight
  5. filtrationThe solid was filtered
  6. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-9d091a2bf819414f88d0120c7abe3c21
Source dataset
uspto-grants-2014_12
Patent number
US08906946B2

Reaction notes

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