Potassium Fluoride → HCID 86596249, compound

HRID 898191Notes

Reaction equation

C1(P(C2CCCCC2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)CCCCC1.[CH:26](C1C=CC(B(O)O)=CC=1)=[O:27].Br[C:38]1[CH:43]=[CH:42][C:41]([O:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])=[C:40]([Cl:53])[CH:39]=1.[F-].[K+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:53][C:40]1[CH:39]=[C:38]([C:17]2[CH:16]=[CH:15][C:14]([C:9]3[C:8]([CH:26]=[O:27])=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:19][CH:18]=2)[CH:43]=[CH:42][C:41]=1[O:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52]

Participants

Conditions

Temperature: 75 °C

Procedure

Palladium acetate (0.005 g, 0.022 mmol) and 2-(dicyclohexylphosphino)biphenyl (0.015 g, 0.044 mmol) were added to a solution of (4-formylphenyl)boronic acid (0.25 g, 1.65 mmol), 1-bromo-3-chloro-4-octoxybenzene (0.35 g, 1.10 mmol, from Step A), and potassium fluoride (0.19 g, 3.30 mmol) in 1,4-dioxane (3 mL). The reaction mixture was heated at 75° C. for 3 h. The reaction was cooled, filtered through celite and concentrated in vacuo. Silica gel chromatography eluting with 1% ethyl acetate/hexane yielded 0.17 g of desired product: 1H NMR (500 MHz, CD3OD): δ 10.01 (s, 1H), 7.97 (d, J=8.0 Hz, 2H), 7.80 (d, J=8.0 Hz, 2H), 7.74 (s, 1H), 7.61 (d, J=7.7 Hz, 1H), 7.16 (d, J=8.7 Hz, 1H) 4.11 (t, J=6.2 Hz, 2H), 1.80-1.89 (m, 2H), 1.50-1.60 (m, 2H), 1.28-1.46 (m, 8H), 0.88-0.97 (m, 3H)

Workup

temperatureThe reaction was cooled
filtrationfiltered through celite and
concentrationconcentrated in vacuo
washSilica gel chromatography eluting with 1% ethyl acetate/hexane

Sources & evidence

ORD record: ord-c1596159f2b946e08bbb22af5791fc11
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07351725B2

Reaction notes

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