Triethylamine → 2-(3,3-Dimethylbut-1-en-2-yl)-2'-fluoro-5'-methoxy-4-((4-methoxybenzyl)oxy)biphenyl

HRID 1049598Notes

Reaction equation

HRID 1049598 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[CH:12][C:11]=1[C:26](O)([C:28]([CH3:31])([CH3:30])[CH3:29])[CH3:27].C(N(CC)CC)C.S(Cl)(Cl)=O>C1(C)C=CC=CC=1>[CH3:29][C:28]([CH3:31])([CH3:30])[C:26]([C:11]1[CH:12]=[C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[CH:14]=[CH:15][C:10]=1[C:3]1[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=1[F:1])=[CH2:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 1177599872-(2'-Fluoro-5'-methoxy-4-((4-methoxybenzyl)oxy)biphenyl-2-yl)-3,3-dimethylbutan-2-ol

Product 1

HCID 1177596802-(3,3-Dimethylbut-1-en-2-yl)-2'-fluoro-5'-methoxy-4-((4-methoxybenzyl)oxy)biphenylYield 87.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-(2′-fluoro-5′-methoxy-4-((4-methoxybenzyl)oxy)biphenyl-2-yl)-3,3-dimethylbutan-2-ol (182 mg) and triethylamine (0.12 mL) in toluene (5 mL) was added thionyl chloride (60 μL), and the mixture was stirred at room temperature for 1 hr. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (153 mg) as a colorless oil.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ebd8c59c08de444a8751f01f00f192a8
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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