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

HRID 502845Notes

Reaction equation

HRID 502845 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-7688fa39bab94122a6c9be36a60b16b2
Source dataset
uspto-grants-2010_08
Patent number
US07776830B2

Reaction notes

Loading…