Thionyl Chloride → 5-Bromo-2-chloromethyl-4-methoxy-3-methyl-benzofuran

HRID 29455Notes

Reaction equation

HRID 29455 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10]O)=[C:7]([CH3:12])[C:6]=2[C:13]=1[O:14][CH3:15].S(Cl)([Cl:18])=O>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][Cl:18])=[C:7]([CH3:12])[C:6]=2[C:13]=1[O:14][CH3:15]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 68711184(5-Bromo-4-methoxy-3-methyl-benzofuran-2-yl)-methanol

Product 1

HCID 687105625-Bromo-2-chloromethyl-4-methoxy-3-methyl-benzofuranYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-bromo-4-methoxy-3-methyl-benzofuran-2-yl)-methanol in 7 mL of dichloromethane was added 0.5 mL of thionyl chloride at room temperature. After 2 h the reaction was concentrated in vacuo, diluted with ethyl acetate and washed with water. The organics were dried over magnesium sulfate, filtered and concentrated in vacuo to give 216 mg (92%) of 5-bromo-2-chloromethyl-4-methoxy-3-methyl-benzofuran. 1H NMR (400 MHz, CDC3) δ ppm 2.4 (s, 3 H) 3.9 (s, 3 H) 4.7 (s, 2 H) 7.1 (d, J=8.8 Hz, 1 H) 7.4 (d, J=8.6 Hz, 1 H).

Workup

  1. concentrationAfter 2 h the reaction was concentrated in vacuo
  2. additiondiluted with ethyl acetate
  3. washwashed with water
  4. dry with materialThe organics were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1c2e16696fc441ceb9f865b7bb700f86
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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