Water → 1-Bromo-3-chloromethyl-2,5-dimethoxy-benzene

HRID 1835995Notes

Reaction equation

HRID 1835995 reaction equation
[Br:1][C:2]1[C:3]([O:12][CH3:13])=[C:4]([CH2:10]O)[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.O=S(Cl)[Cl:16].O>C1COCC1.[Cl-].[Cl-].[Zn+2]>[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([CH2:10][Cl:16])[C:3]=1[O:12][CH3:13]

Participants

6

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 101927773-Bromo-2,5-dimethoxybenzyl Alcohol

Product 1

HCID 103081541-Bromo-3-chloromethyl-2,5-dimethoxy-benzeneYield 75%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 52 (7.5 g, 30 mmol) and ZnCl2 (1 g) in THF (100 ml) was added SOCl2 (5.31 g, 45 mmol) dropwise. After 1 hr at rt, the reaction was poured into water and extracted with ether. The ether was dried, concentrated and the product was purified by column chromatography on silica gel (10% EtOAc/hex) to give 53 as an oil (5.5 g, 75%): 1H NMR(DMSO-d6) δ 7.21(d, 1 H, J=3.0 Hz), 7.08 (d, 1 H, J=3.0 Hz), 4.73 (s, 2 H), 3.78 (s, 3 H), 3.75 (s, 3 H)

Workup

  1. extractionextracted with ether
  2. dry with materialThe ether was dried
  3. concentrationconcentrated
  4. customthe product was purified by column chromatography on silica gel (10% EtOAc/hex)

Sources & evidence

ORD record
ord-3840035076c64a5dbf7ea6b7173dc840
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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