Chlorosulfonic acid → 5-Bromo-2-oxo-2,3-dihydro-1,3-benzoxazole-6-sulfonyl chloride

HRID 920268

Reaction equation

HRID 920268 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[NH:7][C:6]=2[CH:11]=1.[Cl:12][S:13](O)(=[O:15])=[O:14]>C(Cl)Cl>[Br:1][C:2]1[C:3]([S:13]([Cl:12])(=[O:15])=[O:14])=[CH:4][C:5]2[O:9][C:8](=[O:10])[NH:7][C:6]=2[CH:11]=1

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 268532-Benzoxazolinone, 5-bromo-

Product 1

HCID 126110465-Bromo-2-oxo-2,3-dihydro-1,3-benzoxazole-6-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of commercially-available 5-bromobenzo[d]oxazol-2(3H)-one (35-1, 500 mg, 2.336 mmol) in DCM (23 mLl) at RT was added chlorosulfonic acid (1565 μl, 23.36 mmol). The mixture became a solution that was stirred at RT. After 18 h, The solution was cooled to 0° C. and carefully quenched with ice chips and then partitioned between water (15 mL) and EtOAc (150 mL). The aqueous layer was extracted with 3×30 mL DCM. The combined organics were dried over Na2SO4, filtered, concentrated to give 35-2 as a white solid, which was carried forward without further purification.

Workup

  1. temperatureThe solution was cooled to 0° C.
  2. customcarefully quenched with ice chips
  3. custompartitioned between water (15 mL) and EtOAc (150 mL)
  4. extractionThe aqueous layer was extracted with 3×30 mL DCM
  5. dry with materialThe combined organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7a9772516b7644b49473e9d2e760556d
Source dataset
uspto-grants-2016_03
Patent number
US09273040B2

Linked notes

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