Potassium Fluoride → HCID 59691757, compound

HRID 898200Notes

Reaction equation

HRID 898200 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]([OH:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH:3]=1.[CH:16]([C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)=[O:17].[F-].[K+]>O1CCCC1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1>[OH:15][CH:8]([C:4]1[CH:3]=[C:2]([C:21]2[CH:22]=[CH:23][C:18]([CH:16]=[O:17])=[CH:19][CH:20]=2)[CH:7]=[CH:6][CH:5]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

8

Reactant 3

HCID 522689Potassium FluorideHCID 5910734-Formylphenylboronic AcidHCID 62608744HCID 62608744, compound

Product 1

HCID 59691757HCID 59691757, compoundYield 73.9%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 27342162-(Dicyclohexylphosphino)biphenylCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-bromo-3-(1-hydroxyhept-1-yl)benzene (1.00 g, 3.70 mmol, from Step A), 4-formylphenylboronic acid (0.83 g, 5.55 mmol) and potassium fluoride (0.65 g, 11.10 mmol) in tetrahydrofuran (10 mL) was added palladium(II) acetate (0.016 g, 0.071 mmol) and 2-(dicyclohexylphosphino)biphenyl (0.052 g, 0.148 mmol). After stirring for 24 h at rt, the reaction was diluted with ethyl acetate (50 mL), washed with water (50 mL), sat'd sodium chloride (50 mL), dried over magnesium sulfate and concentrated in vacuo. Silica gel chromatography eluting with 25% ethyl acetate/hexanes gave 0.81 g of product as a yellow oil.

Workup

  1. washwashed with water (50 mL), sat'd sodium chloride (50 mL)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. washSilica gel chromatography eluting with 25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-808bc7445d83410f8c2b7ae0985ee0fd
Source dataset
uspto-grants-2008_04
Patent number
US07351725B2

Reaction notes

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