p-Bromochlorobenzene → HCID 10130354, compound

HRID 984669Notes

Reaction equation

HRID 984669 reaction equation
C([N:3]([CH2:13][CH3:14])[C:4](=O)[C:5]1[C:6](=CC=CC=1)O)C.Br[C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].N1CCCCC1.[OH-].[NH4+].CCCCCCCCCCCC>[Cu]I.O.C(OCC)(=O)C.CN(C=O)C>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([N:3]2[CH2:4][CH2:5][CH2:6][CH2:14][CH2:13]2)=[CH:17][CH:18]=1

Participants

11

Reactant 6

HCID 7806p-Bromochlorobenzene2×HCID 8082PiperidineHCID 8182DodecaneHCID 14923Ammonium HydroxideHCID 62657Potassium Phosphate, TribasicHCID 88006Diethylsalicylamide

Product 1

HCID 10130354HCID 10130354, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

CuI (10 mg, 0.05 mmol), N,N-diethylsalicylamide (39 mg, 0.20 mmol), 4-bromochlorobenzene (191 mg, 1.0 mmol) and K3PO4 (425 mg, 2.0 mmol) were put into a screw-capped test tube with a Teflon-lined septum. The tube was then evacuated and backfilled with argon (3 cycles). Piperidine (148 μL, 1.5 mmol) and DMF (0.5 mL) were added by syringes. The reaction mixture was stirred at 90° C. for 20 h. The reaction mixture was allowed to reach room temperature. Ethyl acetate (˜2 mL), water (˜10 mL), ammonium hydroxide (˜0.5 mL) and dodecane (227 μL) were added. The organic phase was analyzed by GC and GC-MS. A 75% conversion of 4-bromochlorobenzene and 29% calibrated GC yield was obtained.

Workup

  1. customThe tube was then evacuated
  2. customto reach room temperature
  3. customyield
  4. customwas obtained

Sources & evidence

ORD record
ord-845154f6b4b3418184b69df2318107cf
Source dataset
uspto-grants-2005_03
Patent number
US06867298B2

Reaction notes

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