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[ CAS No. 115010-11-2 ]

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Chemical Structure| 115010-11-2
Chemical Structure| 115010-11-2
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Product Details of [ 115010-11-2 ]

CAS No. :115010-11-2 MDL No. :MFCD02677703
Formula : C8H7ClO3S Boiling Point : 339.6°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :218.66 g/mol Pubchem ID :2776154
Synonyms :

Safety of [ 115010-11-2 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P280-P303+P361+P353-P301+P330+P331-P304+P340+P310-P305+P351+P338+P310 UN#:3261
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 115010-11-2 ]

  • Upstream synthesis route of [ 115010-11-2 ]
  • Downstream synthetic route of [ 115010-11-2 ]

[ 115010-11-2 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 496-16-2 ]
  • [ 115010-11-2 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With sulfur trioxide-N,N-dimethylformamide complex In 1,2-dichloro-ethane at 85℃; for 1 h;
Stage #2: With thionyl chloride In 1,2-dichloro-ethane at 20 - 75℃; for 1 h;
3.56 g (29.6 mmol) 2,3-dihydrobenzofuran was added to a slurry of 5.44 g (35.5 mmol) sulfur trioxide-N,N-dimethylformamide complex in 12 mL 1,2-dichloroethane under argon. The reaction was heated to 85° C. for 1 hour and then cooled to room temperature. Thionyl chloride (2.6 mL, 35.5 mmol, 1.2 eq) was added dropwise and the reaction was slowly heated over the course of one hour, by which time it had reached 75° C. The mixture was allowed to cool to room temperature and 100 mL of methylene chloride and 100 mL water were added. The organic extract was separated, dried over magnesium sulfate, filtered and evaporated to afford 6.56 g (100percent) of 2,3-dihydrobenzofuran-5-sulfonyl chloride as a tan oil. (TLC Rf chloroform/hexanes=1/1)
100%
Stage #1: With sulfur trioxide-N,N-dimethylformamide complex In 1,2-dichloro-ethane at 85℃; for 1 h;
Stage #2: With thionyl chloride In 1,2-dichloro-ethane at 20 - 75℃; for 1 h;
2,3-Dihydrobenzofuran-5-sulfonyl chloride; Prepared from commercially available 2,3-dihydrobenzofuran as described in the patent EP 0583960A2.3.56 g (29.6 mmol) 2,3-dihydrobenzofuran was added to a slurry of 5.44 g (35.5 mmol) sulfur trioxide-N,N-dimethylformamide complex in 12 mL 1,2-dichloroethane under argon. The reaction was heated to 85° C. for 1 hour and then cooled to room temperature. Thionyl chloride (2.6 mL, 35.5 mmol, 1.2 eq) was added dropwise and the reaction was slowly heated over the course of one hour, by which time it had reached 75° C. The mixture was allowed to cool to room temperature and 100 mL of methylene chloride and 100 mL water were added. The organic extract was separated, dried over magnesium sulfate filtered and evaporated to afford 6.56 g (100percent) of 2,3-dihydrobenzofuran-5-sulfonyl chloride as a tan oil. (TLC Rf chloroform/hexanes=1/1)
91.7% With thionyl chloride In water; N,N-dimethyl-formamide; toluene EXAMPLE 4
Preparation of 2,3-dihydrobenzofuran-5-sulfonyl chloride
Sulfur trioxide-N,N-dimethylformamide complex (9.2 g, 60 mmoles) and N,N-dimethylformamide (20 ml) were added to a 250 ml, 3-necked flask under nitrogen purge.
The solution was stirred at room temperature and 2,3-dihydrobenzofuran (6.0 g, 50 mmoles) was added dropwise.
The solution was slowly heated to 85°-90° C. over the course of one hour.
The light brown solution was allowed to come to room temperature and thionyl chloride (7.2 g, 60 mmoles) was added dropwise.
The mixture was allowed to stir one hour at room temperature.
The solution was slowly heated to 85° C. and was maintained at that temperature for 1 hour.
The solution was allowed to cool to 40° C. Toluene (25 ml) was added to the solution, which was then poured into a mixture of ice and water (50 ml).
Another 25 ml aliquot of toluene was added.
The mixture was stirred for 10 minutes to dissolve any solids and the layers were separated.
The aqueous layer was extracted with toluene (3*25 ml).
The combined toluene layers were washed with water and dried over magnesium sulfate.
The magnesium sulfate was removed and washed with toluene.
The toluene was removed under vacuum, leaving 10.0 g of the title product (91.7percent yield).
Nuclear magnetic resonance assays confirmed the identity of the title compound. FDMS (MeOH) m/e 218 (M+).
Analysis for C8 H7 ClO3 S: Theory: C, 43.94; H, 3.23. Found: C, 44.14; H, 3.24.
23% With chlorosulfonic acid In dichloromethane at 5 - 20℃; INTERMEDIATE 54 2, 3-Dihydro-benzofuran-5-sulfonyl chloride 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 percent).'H NMR 270 MHz (CDC13) 8 ppm 3.32 (t, J=8. 91 Hz, 2 H) 4.75 (t, J=8. 91 Hz, 2 H) 6.90 (d, J=9. 15 Hz, 1 H) 7.78-7. 90 (m, 2 H)
23% With chlorosulfonic acid In dichloromethane at 5 - 20℃; Intermediate 1; 2,3-Dihydro-benzofuran-5-sulfonyl chlorideChlorosulphonic 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 at room temperature over night. The reaction mixture was quenched with water (150 mL) keeping the temperature below 10 °C. The organic phase was separated and washed with aqueous solution OfNaHCO3 (13, 9 g in 150 mL of water). The organic solvents were evaporated giving a solid residue 3.3 g (23 percent). 1H NMR 270 MHz (Chloroform-d) δ ppm 3.32 (t, J=8.91 Hz, 2 H) 4.75 (t, J=8.91 Hz, 2 H) 6.90 (d, J=9.15 Hz, 1 H) 7.78 - 7.90 (m, 2 H).

Reference: [1] Patent: US2005/267074, 2005, A1, . Location in patent: Page/Page column 25; 44
[2] Patent: US2008/227744, 2008, A1, . Location in patent: Page/Page column 12-13
[3] Patent: US6506754, 2003, B1,
[4] Patent: US5387681, 1995, A,
[5] Patent: WO2005/58858, 2005, A1, . Location in patent: Page/Page column 129
[6] Patent: WO2006/62481, 2006, A1, . Location in patent: Page/Page column 27
[7] Patent: US5968942, 1999, A,
[8] Patent: US6046190, 2000, A,
[9] Patent: US6140505, 2000, A,
[10] Patent: US6150556, 2000, A,
[11] Patent: US6143747, 2000, A,
[12] Patent: US5455258, 1995, A,
[13] Patent: US5552419, 1996, A,
[14] Patent: US5506242, 1996, A,
[15] Patent: US5753660, 1998, A,
[16] Patent: US5705500, 1998, A,
[17] Patent: US5776971, 1998, A,
[18] Patent: US6143788, 2000, A,
[19] Patent: US5756533, 1998, A,
[20] Patent: US5968970, 1999, A,
[21] Patent: US6172101, 2001, B2,
[22] Patent: US5985870, 1999, A,
[23] Patent: US2006/293361, 2006, A1, . Location in patent: Page/Page column 3
[24] Patent: US6388132, 2002, B1, . Location in patent: Page column 48
[25] Patent: US6372778, 2002, B1, . Location in patent: Example 180
[26] Patent: US5585397, 1996, A,
[27] Patent: US5783701, 1998, A,
  • 2
  • [ 496-16-2 ]
  • [ 107-06-2 ]
  • [ 115010-11-2 ]
YieldReaction ConditionsOperation in experiment
99% With thionyl chloride In water EXAMPLE 1
Preparation of 2,3-dihydrobenzofuran-5-sulfonyl chloride
To a 250 ml, 3-neck flask under nitrogen purge was added 9.2 grams (60 mmoles) of sulfur trioxide-N,N-dimethylformamide complex and 20 ml of 1,2-dichloroethane.
The slurry was stirred at room temperature and 2,3-dihydrobenzofuran (6.0 g, 50 mmoles) was added dropwise at room temperature.
The slurry was slowly heated to 85° C. and aliquots were monitored for the progress of the reaction.
After one hour the reaction was complete.
The reaction slurry was allowed to come to room temperature, at which time thionyl chloride (7.2 g, 60 mmoles) was added dropwise.
The reaction mixture was slowly heated over the course of one hour, by which time it had reached 75° C.
The mixture was allowed to cool to room temperature.
Water (100 ml) was then added to the slurry.
The aqueous layer was extracted with 1,2-dichloroethane (3*25 ml).
The 1,2-dichloroethane layers were combined and washed with water (25 ml) and dried over magnesium sulfate.
The magnesium sulfate was filtered and washed with 1,2-dichloroethane.
The 1,2-dichloroethane was removed under vacuum to give 11 grams of the title compound (>99percent yield).
Nuclear magnetic resonance assays confirmed the identity of the title compound. FDMS (MeOH) m/e 218 (M+).
Analysis for C8 H7 ClO3 S: Theory: C, 43.94; H, 3.23. Found: C, 44.13; H, 3.34.
Reference: [1] Patent: US5387681, 1995, A,
  • 3
  • [ 115010-11-2 ]
  • [ 869885-60-9 ]
YieldReaction ConditionsOperation in experiment
80% With N-Bromosuccinimide In benzene at 80℃; for 1 h; 2,3-Dihydrobenzofuran-5-sulfonyl chloride 300 mg (1.37 mmol) was dissolved in 2 mL of benzene. N-bromosuccinimide 244 mg (1.37 mmol) and AIBN 3 mg were added to the solution and the reaction was heated at 80° C. for 1 hour. The reaction was allowed to come to room temperature, filtered and the benzene removed under vacuum. The residue was purified by chromatography on silica gel with hexanes/methylene chloride=2/1 to afford 237 mg (80percent) of the pure material (TLC). The final product can be recrystallized from ether/hexanes to provide colorless crystals with m.p. 48.5-50.6° C.;Preparation of benzofuran-5-sulfonyl chloride
2,3-Dihydrobenzofuran-5-sulfonyl chloride 300 mg (1.37 mmol) was dissolved in 2 mL of benzene. N-bromosuccinimide 244 mg (1.37 mmol) and 3 mg AIBN were added to the solution and the reaction was heated at 80° C. for 1 hour.
The reaction was allowed to come to room temperature, filtered and the filtrate was concentrated in vacuo.
The residue was purified by chromatography on silica gel (30percent CH2Cl2/hexanes) to afford 237 mg (80percent yield) of the pure material.
3-Methyl-2,3-dihydrobenzofuran was synthesised as described in the literature starting from 2-iodophenol (Organic Synthesis, CV3, 418; L. W. Menapace and H. G. Kuivila, J. Amer. Chem. Soc., 86, 3047 (1964), and references cited therein).
80% With N-Bromosuccinimide In benzene at 80℃; for 1 h; Benzofuran-5-sulfonyl chloride; 2,3-Dihydrobenzofuran-5-sulfonyl chloride 300 mg (1.37 mmol) was dissolved in 2 mL of benzene. N-bromosuccinimide 244 mg (1.37 mmol) and AIBN 3 mg were added to the solution and the reaction was heated at 80° C. for 1 hour. The reaction was allowed to come to room temperature, filtered and the benzene removed under vacuum. The residue was purified by chromatography on silica gel with hexanes/methylene chloride=2/1 to afford 237 mg (80percent) of the pure material (TLC). The final product can be recrystallized from ether/hexanes to provide colorless crystals with m.p. 48.5-50.6° C.
Reference: [1] Patent: US2005/267074, 2005, A1, . Location in patent: Page/Page column 25; 44
[2] Patent: US2008/227744, 2008, A1, . Location in patent: Page/Page column 13
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