Thionyl Chloride → 4-Benzyloxy-2-chloromethyl-5'-isopropyl-2'-methoxy-biphenyl

HRID 604190Notes

Reaction equation

HRID 604190 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[C:19]([CH:21]([CH3:23])[CH3:22])[CH:18]=[CH:17][C:16]=2[O:24][CH3:25])=[C:11]([CH2:26]O)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:30])=O>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[C:19]([CH:21]([CH3:23])[CH3:22])[CH:18]=[CH:17][C:16]=2[O:24][CH3:25])=[C:11]([CH2:26][Cl:30])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 67087233(4-Benzyloxy-5'-isopropyl-2'-methoxy-biphenyl-2-yl)-methanol

Product 1

HCID 670872924-Benzyloxy-2-chloromethyl-5'-isopropyl-2'-methoxy-biphenyl

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4-Benzyloxy-5′-isopropyl-2′-methoxy-biphenyl-2-yl)-methanol (1.10 g) is dissolved in methylene chloride (10 ml), and thereto is added thionyl chloride (332 μl) and the mixture is stirred at room temperature for 30 minutes. The reaction solution is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (hexane:ethyl acetate=1:0→9:1) to give 4-benzyloxy-2-chloromethyl-5′-isopropyl-2′-methoxy-biphenyl (1.15 g). MS (m/z): 345

Workup

  1. concentrationThe reaction solution is concentrated under reduced pressure
  2. customthe residue is purified by silica gel column chromatography (hexane:ethyl acetate=1:0→9:1)

Sources & evidence

ORD record
ord-004fd657aba14ec68b3273ade9a48071
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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