Water → HCID 86707568, compound

HRID 2279965Notes

Reaction equation

HRID 2279965 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH3:14])[CH:5]=[C:4]([Br:15])[CH:3]=1.[CH2:16]([O:23][CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31](B2OC(C)(C)C(C)(C)O2)=[CH:30][C:29]=1[F:43])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>C1COCC1>[CH2:16]([O:23][CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([C:2]2[CH:7]=[C:6]([O:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH3:14])[CH:5]=[C:4]([Br:15])[CH:3]=2)=[CH:30][C:29]=1[F:43])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 962WaterHCID 86707569HCID 86707569, compoundHCID 86707570HCID 86707570, compound

Product 1

HCID 86707568HCID 86707568, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

17.0 g (50.0 mmol) 1,3-dibromo-5-(2-methoxy-ethoxymethoxy)-benzene, 19.3 g (50.0 mmol) 2-[4-(3-benzyloxy-propoxy)-3-fluoro-phenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane and 41.3 g (150 mmol) sodium metaborate-tetrahydrate are suspended in 200 ml THF and 200 ml water and 1.6 g (2 mmol) palladium(dppf) are added. The mixture is heated overnight at reflux. After partial removal of the solvent and addition of 100 ml MTB ether, the mixture is acidified with 2M hydrochloric acid. The organic layer is separated and the aqueous layer is extracted three times with MTB ether. The combined organic layers are washed with sat. aq. sodium chloride solution, dried over sodium sulfate and the solvent is removed in vacuo. The crude product is filtered through silica gel with toluene/ethylacetate (7:3 to 1:1) to yield 4-(3-benzyloxy-propoxy)-3′-bromo-3-fluoro-5′-(2-methoxy-ethoxymethoxy)-biphenyl as a yellow oil.

Workup

  1. temperatureThe mixture is heated overnight
  2. temperatureat reflux
  3. customAfter partial removal of the solvent and addition of 100 ml MTB ether
  4. customThe organic layer is separated
  5. extractionthe aqueous layer is extracted three times with MTB ether
  6. washThe combined organic layers are washed with sat. aq. sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. customthe solvent is removed in vacuo
  9. filtrationThe crude product is filtered through silica gel with toluene/ethylacetate (7:3 to 1:1)

Sources & evidence

ORD record
ord-3101897ba66c4408a048554a6d820577
Source dataset
uspto-grants-2015_09
Patent number
US09133395B2

Reaction notes

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