Sodium Carbonate → (4'-(Benzyloxy)-2,2',6'-trimethylbiphenyl-3-yl)methanol

HRID 2280655Notes

Reaction equation

HRID 2280655 reaction equation
[CH3:1][C:2]1[C:7](Br)=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][OH:10].[CH2:11]([O:18][C:19]1[CH:24]=[C:23]([CH3:25])[C:22](B(O)O)=[C:21]([CH3:29])[CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>CN(C)C=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH2:11]([O:18][C:19]1[CH:24]=[C:23]([CH3:25])[C:22]([C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([CH2:9][OH:10])[C:2]=2[CH3:1])=[C:21]([CH3:29])[CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 10035697(3-Bromo-2-methylphenyl)methanolHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 23157199(4-(Benzyloxy)-2,6-dimethylphenyl)boronic acid

Product 1

HCID 89701782(4'-(Benzyloxy)-2,2',6'-trimethylbiphenyl-3-yl)methanolYield 57.2%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-Methyl-3-bromo-phenylmethanol (201 mg, 1 mmol, prepared by a method disclosed in PCT patent application WO2010143733), (4-(benzyloxy)-2,6-dimethylphenyl) boronic acid 12b (300 mg, 1.20 mmol), 1 mL of 2M aqueous sodium carbonate solution, 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (33 mg, 0.08 mmol) and tris(dibenzylideneacetone)dipalladium (18 mg, 0.02 mmol) were dissolved in 1 mL of N,N-dimethylformamide. The reaction mixture was reacted at 120° C. under microwave conditions for 1 hour. The resulting mixture was mixed with 10 mL of water and extracted with ethyl acetate (20 mL×2). The combined organic extracts were washed with saturated sodium chloride solution (30 mL), dried with anhydrous magnesium sulphate, and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography with elution system B to obtain the title compound (4′-(benzyloxy)-2,2′,6′-trimethylbiphenyl-3-yl)methanol 12c (190 mg, yield 57.2%) as a red slime.

Workup

  1. customThe reaction mixture was reacted at 120° C. under microwave conditions for 1 hour
  2. extractionextracted with ethyl acetate (20 mL×2)
  3. washThe combined organic extracts were washed with saturated sodium chloride solution (30 mL)
  4. dry with materialdried with anhydrous magnesium sulphate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography with elution system B

Sources & evidence

ORD record
ord-6e7a7ffad3c14926aa54fe3ba7a43d0f
Source dataset
uspto-grants-2015_09
Patent number
US09139548B2

Reaction notes

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