Thionyl Chloride → 2-Chloromethyl-3'-benzyloxybiphenyl

HRID 278177Notes

Reaction equation

HRID 278177 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:21]O)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:25])=O>C(Cl)Cl>[Cl:25][CH2:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:10]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22627088(3'-Benzyloxybiphenyl-2-yl)methanol

Product 1

HCID 226271042-Chloromethyl-3'-benzyloxybiphenyl

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3′-benzyloxybiphenyl-2-yl)methanol from Example 4, Step E (247 mg, 0.851 mmol) in dry CH2Cl2 (5 mL) was added thionyl chloride (1.01 g, 8.51 mmol). The reaction mixture was stirred at ambient temperature for 2 hours, then concentrated to dryness in vacuo. The residue was concentrated twice from cyclohexane in vacuo to yield the titled compound.

Workup

  1. concentrationconcentrated to dryness in vacuo
  2. concentrationThe residue was concentrated twice from cyclohexane in vacuo

Sources & evidence

ORD record
ord-4aacf400d7764c4ebcf40f15133ca138
Source dataset
uspto-grants-2002_03
Patent number
US06358985B1

Reaction notes

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