Acetic Acid → 1-Hydroxydibenzothiophene

HRID 650913Notes

Reaction equation

HRID 650913 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.Br.CC(O)=[O:17]>>[OH:17][C:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 3023Dibenzothiophene

Product 1

HCID 1501301-Hydroxydibenzothiophene

Conditions

Temperature
130 °C

Procedure

To a stirred solution of the dibenzothiophene (0.040 g, 0.19 mmoles) isolated from Step D in HOAc (2.5 mL) was added 40% HBr (0.65 mL, 5.6 mmoles) under N2. The reaction was heated to 130° C. for 20 hrs. The resulting green solution was partitioned between EtOAc and ice/brine. The organic layer was washed with sat. NaHCO3 (2×) and brine. The EtOAc extract was dried over Na2SO4 and concentrated in vacuo to give an off-white solid (0.0366 g). Purification by plate layer chromatography with 1:1 hexane/CH2Cl2 afforded the desired phenol as a white solid (0.0294 g).

Workup

  1. customThe resulting green solution was partitioned between EtOAc and ice/brine
  2. washThe organic layer was washed with sat. NaHCO3 (2×) and brine
  3. extractionThe EtOAc extract
  4. dry with materialwas dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-891d911a0b8644e09109d69ef78b54f0
Source dataset
uspto-grants-2001_08
Patent number
US06277843B1

Reaction notes

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