Dimethylformamide → 1-Bromo-2-(chloromethyl)-4-iodobenzene

HRID 19819Notes

Reaction equation

HRID 19819 reaction equation
S(Cl)([Cl:3])=O.[Br:5][C:6]1[CH:11]=[CH:10][C:9]([I:12])=[CH:8][C:7]=1[CH2:13]O.CN(C=O)C>ClCCl>[Br:5][C:6]1[CH:11]=[CH:10][C:9]([I:12])=[CH:8][C:7]=1[CH2:13][Cl:3]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 53424372(2-Bromo-5-iodophenyl)methanol

Product 1

HCID 593463281-Bromo-2-(chloromethyl)-4-iodobenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (13 mL) is added to a suspension of 4-bromo-3-hydroxymethyl-1-iodo-benzene (47.0 g) in dichloromethane (100 mL) containing DMF (0.1 mL). The mixture is stirred at ambient temperature for 3 h. Then, the solvent and the excess reagent is removed under reduced pressure. The residue is triturated with methanol and dried.

Workup

  1. customThen, the solvent and the excess reagent is removed under reduced pressure
  2. customThe residue is triturated with methanol
  3. customdried

Sources & evidence

ORD record
ord-e5567449752e4d15be6790955f57f084
Source dataset
uspto-grants-2010_06
Patent number
US07745414B2

Reaction notes

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