Dimethylformamide → HCID 22012209, compound

HRID 378547Notes

Reaction equation

HRID 378547 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH2:8][CH:7]([CH2:10][CH2:11][CH2:12]O)[C:6]=2[CH:14]=1.CN(C)C=O.S(Cl)([Cl:22])=O>ClCCl>[Cl:22][CH2:12][CH2:11][CH2:10][CH:7]1[C:6]2[CH:14]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[O:9][CH2:8]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 22012189HCID 22012189, compound

Product 1

HCID 22012209HCID 22012209, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(2,3-Dihydro-5-fluoro-benzofuran-3-yl)-1-propanol, prepared as described in EXAMPLE 11, (51 g) was dissolved in 300 ml of dichloromethane and 0.5 ml of dimethyl formamide was added. During 20 min 50 ml of thionyl chloride was added dropwise followed by stirring for 3 h. Ice cold water was added, the organic phase separated, dried over magnesium sulfate and concentrated in vacuo giving 46 g of 3-(3-chloro-1-propyl)-2,3-dihydro-5-fluoro-benzofuran as an oil.

Workup

  1. additionIce cold water was added
  2. customthe organic phase separated
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aff8dfea0b3d43e3a7020a2f4545a743
Source dataset
uspto-grants-2000_02
Patent number
US06031099

Reaction notes

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