1-Bromo-4-iodobenzene → (E)-2-(4-bromo-phenyl)-3-cyclopentyl-prop-2-en-1-ol

HRID 2103630Notes

Reaction equation

HRID 2103630 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[CH:9]1(/[CH:14]=[C:15](\B2OC(C)(C)C(C)(C)O2)/[CH2:16][OH:17])[CH2:13][CH2:12][CH2:11][CH2:10]1.[F-].[Cs+]>C1COCC1.C1(P([Pd-4](P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[C:15](=[CH:14]\[CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)/[CH2:16][OH:17])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 115221-Bromo-4-iodobenzeneHCID 25953Cesium fluorideHCID 67084716(E)-3-cyclopentyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol

Product 1

HCID 67084705(E)-2-(4-bromo-phenyl)-3-cyclopentyl-prop-2-en-1-olYield 39.7%

Reagents, catalysts & solvents 2

HCID 178420553HCID 178420553, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

According to the procedure described for example 26b the use of 4-bromo-1-iodo-benzene (1.42 g, 5.0 mmol), (E)-3-cyclopentyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol (1.01 g, 4.00 mmol), caesium fluoride (2.28 g, 15.0 mmol) and tetrakis(triphenylphosphino)palladium(0) (577 mg, 500 μmol) in 120 mL THF with heating to 60° C. for 16 h gives a brown oil. Purify the crude product by column chromatography, eluting with a gradient from 100:0 to 60:40 hexanes:ethyl acetate to obtain (E)-2-(4-bromo-phenyl)-3-cyclopentyl-prop-2-en-1-ol (446 mg) as a yellow oil. MS (m/e): 263 {[(79Br)M−H2O]+H}, 265 {[(81Br)M−H2O]+H}.

Workup

  1. customgives a brown oil
  2. customPurify the crude product by column chromatography
  3. washeluting with a gradient from 100:0 to 60:40 hexanes

Sources & evidence

ORD record
ord-b1a52e6371564166ba1c72e53b7c55c5
Source dataset
uspto-grants-2009_08
Patent number
US07576108B2

Reaction notes

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