Triethylamine → 1-Chloro-2-(2-fluoro-phenylethynyl)-4-nitro-benzene

HRID 1038008Notes

Reaction equation

C(N(CC)CC)C.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1I.[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[F:27])#[CH:20]>CN(C)C=O.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[C:20]#[C:19][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[F:27]

Participants

Conditions

Temperature: 70 °C

Procedure

Triethylamine (0.2 ml, 1.43 mmol) was added to a suspension of 1-Chloro-2-iodo-4-nitro-benzene 69 (Step 1) (100 mg, 0.354 mmol), 1-ethynyl-2-fluorobenzene (100 mg, 0.832 mmol), copper iodide (100 mg, 0.525 mmol), Pd(PPh3)2Cl2 (100 mg, 0.142 mmol) in dimethylformamide (2 ml) at room temperature, then stirred at 70° C. for 2 hours. Reaction was cooled to room temperature and extracted with ether (50 ml), washed with water (20 ml), dried (MgSO4), filtered and solvent evaporated yielding a residue which chromatographed on silica gel eluting with 20% v/v MeCl2/hexanes yielding title product 70 as pale yellow solid (80 mg, 82%).

Workup

customReaction
temperaturewas cooled to room temperature
extractionextracted with ether (50 ml)
washwashed with water (20 ml)
dry with materialdried (MgSO4)
filtrationfiltered
customsolvent evaporated
customyielding a residue which
customchromatographed on silica gel eluting with 20% v/v MeCl2/hexanes yielding title product 70 as pale yellow solid (80 mg, 82%)

Sources & evidence

ORD record: ord-328e6b54522445f9b3c7ee502477aaec
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546404B2

Reaction notes

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