Thionyl Chloride → 4-(Chloromethyl)-2'-fluoro-5'-(methyloxy)-2-cyclooctyl-1,1'-biphenyl

HRID 1662397Notes

Reaction equation

HRID 1662397 reaction equation
[CH:1]1([C:9]2[CH:14]=[C:13]([CH2:15]O)[CH:12]=[CH:11][C:10]=2[C:17]2[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:18]=2[F:25])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:28])=O>C(Cl)Cl.CN(C=O)C>[Cl:28][CH2:15][C:13]1[CH:12]=[CH:11][C:10]([C:17]2[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:18]=2[F:25])=[C:9]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]2)[CH:14]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 57706668(2-Cyclooctyl-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methanol

Product 1

HCID 577060514-(Chloromethyl)-2'-fluoro-5'-(methyloxy)-2-cyclooctyl-1,1'-biphenylYield 95%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 66.16F (0.130 g, 0.4 mmol) in DCM (2.00 mL) and DMF (0.03 mL) at 0° C. was added thionyl chloride (0.06 mL, 0.8 mmol). The reaction was stirred at room temperature for 2 hours. After which, the reaction was concentrated in vacuo and the product was then purified on silica gel (0-10% EtOAc in hexanes) to yield 66.16G as a colorless oil (0.130 g, 95% yield).

Workup

  1. concentrationAfter which, the reaction was concentrated in vacuo
  2. customthe product was then purified on silica gel (0-10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-af167c8cf26a4fcc95f766f291c31fb7
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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