Thionyl Chloride → 4,6-Dichloro-2-(chloromethyl)benzofuran

HRID 710303Notes

Reaction equation

HRID 710303 reaction equation
[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([CH2:11]O)[O:10][C:6]=2[CH:5]=[C:4]([Cl:13])[CH:3]=1.CCN(C(C)C)C(C)C.O=S(Cl)[Cl:25]>C1COCC1.CCOCC>[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([CH2:11][Cl:25])[O:10][C:6]=2[CH:5]=[C:4]([Cl:13])[CH:3]=1

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 65440707(4,6-Dichlorobenzofuran-2-yl)methanol

Product 1

HCID 667262474,6-Dichloro-2-(chloromethyl)benzofuranYield 96.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of Step E (0.24 g; 1.1 mmol) and DIPEA (0.2 ml; 1.11 mmol) in anhydrous THF (1 ml), SOCl2 (0.1 ml; 1.13 mmol) was added drop wise at 0° C. under N2 with stirring. The mixture was allowed to warm up to room temperature and stirred overnight, then diluted to 15 ml with Et2O and washed with 0.1N HCl, 5% NaHCO3, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure to give the title compound (0.25 g; 96%), as a creamy syrup, which was used in the next step without further purification. 1H-NMR (CDCl3) 4.68 (s, 2H); 6.8 (s, 1H), 7.2 (s, 1H); 7.39 (s, 1H).

Workup

  1. stirringstirred overnight
  2. washwashed with 0.1N HCl, 5% NaHCO3, brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-98a8f235d60f4ce6867c1782e58cded5
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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