2-Bromo-4-chlorophenol → HCID 18182812, compound

HRID 1359240Notes

Reaction equation

HRID 1359240 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:13][CH3:14])[CH:9]=2)[CH:4]=1)#[CH:2].Br[C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[OH:23]>C(N(CC)CC)C.C(NCC)C.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:22][C:20]1[CH:19]=[CH:18][C:17]2[O:23][C:1]([C:3]3[CH:12]=[CH:11][C:10]4[C:5](=[CH:6][CH:7]=[C:8]([O:13][CH3:14])[CH:9]=4)[CH:4]=3)=[CH:2][C:16]=2[CH:21]=1

Participants

7

Reactant 2

HCID 696702-Bromo-4-chlorophenolHCID 45865222-Ethynyl-6-methoxynaphthalene

Product 1

HCID 18182812HCID 18182812, compoundYield 64.8%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8021DiethylamineSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 2-ethynyl-6-methoxynaphthalene (1.82 g, 10 mmol), 2-bromo-4-chlorophenol (2.01 g, 10 mmol), copper (I) iodide (0.1 g, 0.52 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol) in triethylamine (10 mL) and diethylamine (10 mL) was heated at reflux for 1 hour under an atmosphere of nitrogen then cooled to room temperature. The solid was collected by filtration, washed with ether and dried to give the title compound as a solid (2.0 g). 1HNMR (300 MHz, DMSO-d6): δ8.4 (s, 1H), 8.0-7.9 (m, 3H), 7.75 (d, 1H, J=1.8 Hz), 7.69 (d, 1H, J=9.2 Hz), 7.46 (s, 1H), 7.38-7.32 (m, 2H), 7.24 (dd, 1H, J=9.2, 1.8 Hz), and 3.9 ppm (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour under an atmosphere of nitrogen
  3. filtrationThe solid was collected by filtration
  4. washwashed with ether
  5. customdried

Sources & evidence

ORD record
ord-81f0c94d37e74b1cb0c4d2bda2c49b2b
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

Loading…