Diethyl Ether → 2,2'-Difluoro-4''-(3-hydroxypropyl)[1,1';4',1'']-terphenyl-4-ol

HRID 1530173Notes

Reaction equation

HRID 1530173 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][OH:17])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[F:18].[F:19][C:20]1[CH:21]=[C:22]([OH:35])[CH:23]=[CH:24][C:25]=1B1OC(C)(C)C(C)(C)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>[F:19][C:20]1[CH:21]=[C:22]([OH:35])[CH:23]=[CH:24][C:25]=1[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][OH:17])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[F:18]

Participants

7

Reactant 3

HCID 3283Diethyl EtherHCID 547590983-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 67195875HCID 67195875, compound

Product 1

HCID 671948862,2'-Difluoro-4''-(3-hydroxypropyl)[1,1';4',1'']-terphenyl-4-ol

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

16.5 g (59 mmol) of sodium metaborate octahydrate and 1.3 g (1.8 mmol) of bis(triphenylphosphine)palladium(II) chloride are initially introduced in 150 ml of water and 50 ml of THF, 12.5 g (38.5 mmol) of 3-(4′-bromo-3′-fluorobiphenyl-4-yl)propan-1-ol are added, and a solution of 12.5 g (0.053 mol) of 3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenol in 50 ml of 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, the solvent is removed in vacuo, and the crude product is recrystallised from toluene/ethyl acetate (9:1), giving 2,2′-difluoro-4″-(3-hydroxypropyl)[1,1′;4′,1″]-terphenyl-4-ol as colourless crystals.

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
  6. customthe crude product is recrystallised from toluene/ethyl acetate (9:1)

Sources & evidence

ORD record
ord-1944c11e1a81444584f9066aae90dd51
Source dataset
uspto-grants-2015_07
Patent number
US09090822B2

Reaction notes

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