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

HRID 1038349Notes

Reaction equation

HRID 1038349 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-a212c4325e9043fb8a7a41eaedec2983
Source dataset
uspto-grants-2013_10
Patent number
US08551957B2

Reaction notes

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