1,2-Dibromoethane → 8-(2-Bromoethoxy)-3,4-dihydro-2H-1-benzothiopyran

HRID 1491802Notes

Reaction equation

HRID 1491802 reaction equation
[S:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[OH:11])[CH2:4][CH2:3][CH2:2]1.[Br:12][CH2:13][CH2:14]Br.[OH-].[Na+]>>[Br:12][CH2:13][CH2:14][O:11][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[S:1][CH2:2][CH2:3][CH2:4]2

Participants

4

Reactant 3

HCID 78391,2-DibromoethaneHCID 14798Sodium Hydroxide2×HCID 1216173,4-dihydro-2H-1-benzothiopyran-8-ol

Product 1

HCID 152958328-(2-Bromoethoxy)-3,4-dihydro-2H-1-benzothiopyranYield 32%

Conditions

Temperature
100 °C

Procedure

1 g (6.015 mmol) of 8-thiochromanol is dissolved in 2.26 g (12.03 mmol) of 1,2-dibromoethane. 5.6 cm3 of a 1.6N NaOH solution are added dropwise. The mixture is heated to 100° C.; after 2 hours, the solution reaches pH 7. The mixture is allowed to cool. 100 cm3 of a 2N NaOH solution are added. The mixture is extracted with CH2Cl2 and then dried over MgSO4. Purification over a silica column (eluant: petroleum ether/CH2Cl2 2:1) yields the desired compound.

Workup

  1. temperatureto cool
  2. extractionThe mixture is extracted with CH2Cl2
  3. dry with materialdried over MgSO4
  4. customPurification over a silica column (eluant: petroleum ether/CH2Cl2 2:1)

Sources & evidence

ORD record
ord-29aa67475635469ba6be2f4afeadcc41
Source dataset
uspto-grants-1994_12
Patent number
US05371103

Reaction notes

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