Toluene → HCID 57552550, compound

HRID 1513859Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7][CH2:6]2.Br[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=1.[CH3:22][C:23](C)([O-:25])[CH3:24].[Na+].[C:28]1(C)[CH:33]=CC=C[CH:29]=1>Cl.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[F:21][C:17]1[CH:16]=[C:15]([C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=3)[C:9]=2[O:13][C:28]2[CH:33]=[CH:24][C:23]([OH:25])=[CH:22][CH:29]=2)[CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 115 °C

Procedure

Charge an oven-dried 250 mL round-bottom flask with 6-methoxy-1-tetralone (3.0 g, 17.0 mmol.) and place under nitrogen. Dissolve the solid in toluene (30 mL) and add 1-bromo-3-fluorobenzene (4.7 mL, 42.6 mmol), sodium t-butoxide (6.5 g, 68.1 mmol), palladium acetate (76 mg, 0.34 mmol), and racemic BINAP (212 mg, 0.34 mmol). Heat the solution to 115° C. and stir for 18 hours. Dilute the solution with cold 5N HCl (50 mL) and ethyl acetate (200 mL). Separate the organic layer and dry over sodium sulfate, filter over a pad of celite and concentrate in vacuo. Purify the crude product using radial chromatography to give 3.4 g (74%) of the title compound. This material is used without further purification: mass spectrum (ion spray) m/z=267 (M−H).

Workup

customSeparate the organic layer
dry with materialdry over sodium sulfate
filtrationfilter over a pad of celite
concentrationconcentrate in vacuo
customPurify the crude product

Sources & evidence

ORD record: ord-45933a8dafc24523a2f758729d738356
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217032B2

Reaction notes

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