Thionyl Chloride → 4-(1-Chloropentyl)-4'-(trifluoromethyl)biphenyl

HRID 1391750Notes

Reaction equation

HRID 1391750 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH:15](O)[CH2:16][CH2:17][CH2:18][CH3:19])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.S(Cl)([Cl:25])=O>C(Cl)Cl>[Cl:25][CH:15]([C:12]1[CH:13]=[CH:14][C:9]([C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:22])([F:21])[F:1])=[CH:4][CH:5]=2)=[CH:10][CH:11]=1)[CH2:16][CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 596742571-[4'-(Trifluoromethyl)-4-biphenylyl]-1-pentanol

Product 1

HCID 586298384-(1-Chloropentyl)-4'-(trifluoromethyl)biphenylYield 94.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[4′-(trifluoromethyl)-4-biphenylyl]-1-pentanol (250 mg, 0.81 mmol) in dry DCM (15 mL) under nitrogen at 0° C. (ice/water bath) was added thionyl chloride (590 μL, 8.09 mmol) drop-wise. After stirring the mixture for 30 minutes at rt under nitrogen, the reaction was quenched by cautious addition of saturated aqueous NaHCO3 (20 mL) and extracted with DCM (3×30 mL). The organic extract was separated, washed with brine, dried (MgSO4) and the solvents removed under vacuum to afford the title compound as a yellow gum (251 mg).

Workup

  1. customthe reaction was quenched by cautious addition of saturated aqueous NaHCO3 (20 mL)
  2. extractionextracted with DCM (3×30 mL)
  3. extractionThe organic extract
  4. customwas separated
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. customthe solvents removed under vacuum

Sources & evidence

ORD record
ord-c3c8f86321464d7aac061265592ca6f6
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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