Thionyl Chloride → 4'-(Chloromethyl)-6-fluoro-2'-((1R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-en-2-yl)-1,1'-biphenyl-3-yl methyl ether

HRID 1662393Notes

Reaction equation

HRID 1662393 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]([CH2:16]O)=[CH:12][C:11]=1[C:18]1[C@@:19]2([CH3:27])[C:24]([CH3:26])([CH3:25])[C@@H:22]([CH:23]=1)[CH2:21][CH2:20]2.S(Cl)([Cl:30])=O>C(Cl)Cl.CN(C=O)C>[CH3:9][O:8][C:5]1[CH:4]=[C:3]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][Cl:30])=[CH:12][C:11]=2[C:18]2[C@@:19]3([CH3:27])[C:24]([CH3:26])([CH3:25])[C@@H:22]([CH:23]=2)[CH2:21][CH2:20]3)[C:2]([F:1])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 57706974(2'-Fluoro-5'-(methyloxy)-2-((1R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-en-2-yl)-1,1'-biphenyl-4-yl)methanol

Product 1

HCID 577071654'-(Chloromethyl)-6-fluoro-2'-((1R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-en-2-yl)-1,1'-biphenyl-3-yl methyl etherYield 95%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 66.15F (0.035 g, 0.10 mmol) in DCM (2.00 mL) and DMF (0.01 mL) at 0° C. was added thionyl chloride (0.01 g, 0.10 mmol). The reaction was then stirred at room temperature for 2 hours and was then concentrated in vacuo. The resulting product was then purified on silica gel (0-10% EtOAc in hexanes) to yield 66.15G as a colorless oil (0.035 g, 95% yield).

Workup

  1. concentrationwas then concentrated in vacuo
  2. customThe resulting product was then purified on silica gel (0-10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-368d4acef3564f029c6cad1df277215f
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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