Diethyl Ether → HCID 67195875, compound

HRID 1530172Notes

Reaction equation

HRID 1530172 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][C:3]=1[F:9].CC1(C)C(C)(C)OB([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][OH:27])=[CH:20][CH:19]=2)O1.CCOCC>O.C1COCC1.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>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][OH:27])=[CH:20][CH:19]=2)=[CH:4][C:3]=1[F:9]

Participants

7

Reactant 3

HCID 3283Diethyl EtherHCID 27250061-Bromo-2-fluoro-4-iodobenzeneHCID 586855993-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propan-1-ol

Product 1

HCID 67195875HCID 67195875, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

18 g (65 mmol) of sodium metaborate octahydrate and 2.8 g (3.9 mmol) of bis(triphenylphosphine)palladium(II) chloride are initially introduced in 200 ml of water and 100 ml of THF, 1-bromo-2-fluoro-4-iodobenzene are added, and a solution of 21.5 g (0.082 mol) of 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propan-1-ol in 100 ml THF is subsequently added dropwise. The batch is heated under reflux overnight, taken up in MTB ether and washed three times with water. The org. phase is dried over sodium sulfate, and the solvent is removed in vacuo. Chromatography of the crude product on silica gel with toluene/ethyl acetate (7:1) gives 3-(4′-bromo-3′-fluorobiphenyl-4-yl)propan-1-ol as a colourless oil.

Workup

  1. temperatureThe batch is heated
  2. temperatureunder reflux overnight
  3. washwashed three times with water
  4. dry with materialphase is dried over sodium sulfate
  5. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-effd202c224940a2a5451be7e505ed88
Source dataset
uspto-grants-2015_07
Patent number
US09090822B2

Reaction notes

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