Hydrochloric Acid → HCID 59382908, compound

HRID 1254327Notes

Reaction equation

HRID 1254327 reaction equation
[F:1][C:2]1([F:8])[CH2:5][CH:4]([CH2:6][OH:7])[CH2:3]1.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1.C(N(CC)CC)C.Cl>C(Cl)Cl>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([O:7][CH2:6][CH:4]2[CH2:5][C:2]([F:8])([F:1])[CH2:3]2)(=[O:18])=[O:17])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7396p-Bromobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 45480377(3,3-Difluorocyclobutyl)methanol

Product 1

HCID 59382908HCID 59382908, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A round bottom flask was charged with (3,3-difluorocylobutyl)methanol (1.0 g, 8.2 mmol, 1.0 equiv), 4-bromobenzenesulphonyl chloride (2.2 g, 8.6 mmol, 1.05 equiv) and CH2Cl2 (50 mL). The mixture was cooled to 0° C. and triethylamine (2.07 g, 2.89 mL, 20.5 mmol, 2.5 equiv) was added via syringe. The mixture stirred for 12 h with warming to rt. After this time 1.0 M aq HCl (50 mL) was added. The layers were separated, the organic layer was extracted with CH2Cl2 (50 mL) and the combined organic layers were washed with brine, dried over Na2SO4, filtered and evaporated. The compound was purified by flash chromatography on silica, eluting with 0-30% EtOAc in hexanes. This afforded (3,3-difluorocyclobutyl)methyl 4-bromobenzenesulfonate (2.7 g, 95%) as an off white solid.

Workup

  1. temperaturewith warming to rt
  2. customThe layers were separated
  3. extractionthe organic layer was extracted with CH2Cl2 (50 mL)
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe compound was purified by flash chromatography on silica
  9. washeluting with 0-30% EtOAc in hexanes

Sources & evidence

ORD record
ord-9d65cd3d8c354f2487e7d35b4ea1f410
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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