1-(Difluoromethoxy)-4-ethynylbenzene → HCID 59305294, compound

HRID 2241004Notes

Reaction equation

HRID 2241004 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)[CH2:5][C:6]1[O:7][CH:8]=[CH:9][CH:10]=1.[F:14][CH:15]([F:25])[O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]#[CH:24])=[CH:19][CH:18]=1>C(N(CC)CC)C.[Cu](I)I.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:14][CH:15]([F:25])[O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]#[C:24][C:2]2[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=2)[CH2:5][C:6]2[O:7][CH:8]=[CH:9][CH:10]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 2

HCID 27784971-(Difluoromethoxy)-4-ethynylbenzeneHCID 59305342HCID 59305342, compound

Product 1

HCID 59305294HCID 59305294, compoundYield 61.1%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8471TriethylamineSolvent

Procedure

To a CEM snap top microwave vial (10 ml) equipped with a magnetic stir bar (3×10 mm) was added 2-(3-bromobenzyl)furan (385 mg, 1.62 mmol) in triethylamine (1.5 mL). Copper iodide (80 mg, 0.40 mmol), Tetrakis(triphenylphosphine) palladium (140 mg, 0.121 mmol) and 1-(difluoromethoxy)-4-ethynylbenzene (0.270 mg, 1.60 mmol) were added at room temperature. The reaction was capped and irradiated in a CEM Explorer microwave at 80° C. for 30 minutes then forced air-cooled. The crude material was loaded onto silica gel. Purification by chromatography (2% EtOAc in hexanes) afforded 0.317 gm of an oil (61%). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.99 (s, 2H) 6.16 (dd, J=3.1, 0.8 Hz, 1H) 6.37 (dd, J=3.1, 2.0 Hz, 1H) 7.21 (d, J=8.8 Hz, 2H) 7.28 (ddd, J=7.5, 1.6, 1.6 Hz, 1H) 7.31 (t, J=73.7 Hz, 1H) 7.34-7.42 (m, 3H) 7.53 (dd, J=1.9, 0.7 Hz, 1H) 7.61 (d, J=9.0 Hz, 2H); MS (EI) m/z 324.0 [M+·].

Workup

  1. customTo a CEM snap top microwave vial (10 ml) equipped with a magnetic stir bar (3×10 mm)
  2. customThe reaction was capped
  3. customirradiated in a CEM Explorer microwave at 80° C. for 30 minutes
  4. temperaturethen forced air-cooled
  5. customPurification by chromatography (2% EtOAc in hexanes)

Sources & evidence

ORD record
ord-643da2e418414c5ea910ef184d124e82
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

Loading…