Dihydrobenzofuran → 2,3-Dihydrobenzofuran-5-sulfonyl Chloride

HRID 1162033Notes

Reaction equation

HRID 1162033 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[O:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7]1>C(Cl)Cl>[O:6]1[C:10]2[CH:11]=[CH:12][C:13]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:14][C:9]=2[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 10329DihydrobenzofuranHCID 24638Chlorosulfonic acid

Product 1

HCID 27761542,3-Dihydrobenzofuran-5-sulfonyl Chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Chlorosulphonic acid (43.4 g, 0.366 mol) in DCM (10 mL) was added to a cold solution (5° C.) of 2,3-dihydrobenzofuran (20 g, 0.166 mol) in DCM (200 mL). After the addition the reaction was left with stirring at room temperature overnight. The reaction mixture was quenched with water (150 mL) keeping the temperature below 10° C. The organic phase was separated and washed with an aqueous solution of NaHCO3 (13.9 g dissolved in 150 mL of water). The organic solvents were evaporated to yield the title compound as a solid residue 3.3 g (23%). 1H NMR 270 MHz (CDCl3) δ ppm 3.32 (t, J=8.91 Hz, 2H) 4.75 (t, J=8.91 Hz, 2H) 6.90 (d, J=9.15 Hz, 1H) 7.78-7.90 (m, 2H)

Workup

  1. additionAfter the addition the reaction
  2. waitwas left
  3. customThe reaction mixture was quenched with water (150 mL)
  4. customthe temperature below 10° C
  5. customThe organic phase was separated
  6. washwashed with an aqueous solution of NaHCO3 (13.9 g dissolved in 150 mL of water)
  7. customThe organic solvents were evaporated

Sources & evidence

ORD record
ord-1c01fc22422b42b68e2168cc1a1b6be6
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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