Water → 4-Bromo-thianthren-1-ol

HRID 33795Notes

Reaction equation

HRID 33795 reaction equation
[C:1]1([OH:15])[C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[Br:16]Br.O>C(O)(=O)C>[Br:16][C:4]1[C:5]2[S:6][C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[S:13][C:14]=2[C:1]([OH:15])=[CH:2][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 21569430Thianthren-1-ol

Product 1

HCID 597974464-Bromo-thianthren-1-ol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Thianthren-1-ol (6.5 g, 27.98 mmol) was dissolved in glacial acetic acid (100 ml) and to this solution was added bromine (17.1 μl, 13.99 mmol) in a dropwise fashion over 30 minutes. Water (200 ml) was added to the amber solution and the mixture extracted with EtOAc (3×100 ml). The combined organic extracts were then washed with saturated potassium bicarbonate solution (3×100 ml), dried using MgSO4, filtered and concentrated in vacuo to give the title compound. (7.56 g, 87%). m/z (LC-MS, ESP):, RT=4.92 min, (M++1)=309.

Workup

  1. extractionthe mixture extracted with EtOAc (3×100 ml)
  2. washThe combined organic extracts were then washed with saturated potassium bicarbonate solution (3×100 ml)
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-806b5bbbada74336bdda5ebd6120fccc
Source dataset
uspto-grants-2008_09
Patent number
US07429660B2

Reaction notes

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