1,2-Dibromoethane → 2,3-Dihydro-1,4-benzoxathiin-6-ol

HRID 1246621

Reaction equation

HRID 1246621 reaction equation
Br[CH2:2][CH2:3]Br.C([O-])([O-])=O.[K+].[K+].[SH:11][C:12]1[CH:17]=[C:16]([OH:18])[CH:15]=[CH:14][C:13]=1[OH:19]>CC(C)=O>[O:19]1[C:13]2[CH:14]=[CH:15][C:16]([OH:18])=[CH:17][C:12]=2[S:11][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 27361672-Mercaptobenzene-1,4-diol

Product 1

HCID 125159102,3-Dihydro-1,4-benzoxathiin-6-olYield 55.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

1,2-Dibromoethane (2.3 mL, 26.7 mmol) and K2CO3 (8.21 g, 59.4 mmol) were slurried in acetone (250 mL) and a solution of 2-sulfanyl-1,4-benzenediol (prepared according to J. Org. Chem. 1990, 55, 2736) (4.22 g, 29.7 mmol) in acetone (50 mL) was added over 4 h to the stirred mixture. Once the addition was complete stirring was continued for a further 10 h before the solvent was removed in vacuo. The residue was partitioned between water (50 mL) and EtOAc (50 mL), the aqueous layer was extracted with EtOAc (50 mL) and the combined organic layers were dried (MgSO4) and evaporated. Purification of the residue by column chromatography [SiO2; 9:1 (pentane/EtOAc)] gave the title compound (2.48 g, 55%) as a pale orange oil; δH (CDCl3, 400 MHz) 3.08 (2H, m), 4.31 (2H, m), 4.44 (1H, s), 6.42 (1H, d), 6.49 (1H, s), 6.66 (1H, d); MS m/z (ES−) 167 (M−H+).

Workup

  1. additionOnce the addition
  2. customwas removed in vacuo
  3. customThe residue was partitioned between water (50 mL) and EtOAc (50 mL)
  4. extractionthe aqueous layer was extracted with EtOAc (50 mL)
  5. dry with materialthe combined organic layers were dried (MgSO4)
  6. customevaporated
  7. customPurification of the residue by column chromatography [SiO2; 9:1 (pentane/EtOAc)]

Sources & evidence

ORD record
ord-31422edad81740f2b974eb9bb032f709
Source dataset
uspto-grants-2006_10
Patent number
US07129234B2

Linked notes

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