Dichloromethane → Biphenyl

HRID 1662373Notes

Reaction equation

HRID 1662373 reaction equation
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=2[F:17])=[C:5]([C@@H:18]2[CH2:22][CH2:21][CH2:20][C:19]2([CH3:24])[CH3:23])[CH:4]=1.ClC[C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[C:37](OC)[CH:36]=[CH:35][C:34]=2F)=[C:29]([C@H]2CCCC2(C)C)[CH:28]=1.CC1(C)CCC[C@H]1C1C=C(CO)C=CC=1C1C=C(OC)C=CC=1F.CC1(C)CCC[C@@H]1C1C=C(CO)C=CC=1C1C=C(OC)C=CC=1F.C(Cl)Cl.S(Cl)(Cl)=O>CN(C=O)C>[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=2[F:17])=[C:5]([C@@H:18]2[CH2:22][CH2:21][CH2:20][C:19]2([CH3:24])[CH3:23])[CH:4]=1.[C:30]1([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:31]=[CH:32][CH:27]=[CH:28][CH:29]=1

Participants

9

Reactant 6

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 57705543HCID 57705543, compoundHCID 57705612HCID 57705612, compoundHCID 57705687HCID 57705687, compoundHCID 57705700HCID 57705700, compound

Product 2

HCID 7095BiphenylYield 92%HCID 57705612HCID 57705612, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

4-(Chloromethyl)-2-((1R)-2,2-dimethylcyclopentyl)-2′-fluoro-5′-(methyloxy)-1,1′-biphenyl or 4-(chloromethyl)-2-((1S)-2,2-dimethylcyclopentyl)-2′-fluoro-5′-(methyloxy)-1,1′-biphenyl (66.6O or 66.6P). To a stirred solution of (2-((1R)-2,2-dimethylcyclopentyl)-2′-fluoro-5′-(methyloxy)-1,1′-biphenyl-4-yl)methanol or (2-((1S)-2,2-dimethylcyclopentyl)-2′-fluoro-5′-(methyloxy)-1,1′-biphenyl-4-yl)methanol (66.6AG or 66.6AH) (23.66 g, 72 mmol) in DCM (360 mL, 72 mmol) and DMF (0.56 mL, 7.2 mmol) at 0° C. was added thionyl chloride (11 mL, 144 mmol). Stirring was continued at room temperature for 1 hour. The reaction as then concentrated in vacuo, and the residue was purified on silica gel (0-10% EtOAc in hexanes) to yield 66.6O or 66.6P as a colorless oil (23.0 g, 92% yield). MS ESI (pos.) m/e: 364.1 (M+H2O)+.

Workup

  1. customThe reaction
  2. concentrationas then concentrated in vacuo
  3. customthe residue was purified on silica gel (0-10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-e0e189f90bab4210a3dd640860d65dd2
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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