Sulfolane → HCID 13151860, compound

HRID 485428Notes

Reaction equation

HRID 485428 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:11](Br)[CH2:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[S:7][C:6]=2[CH:17]=1.S1(CCCC1)(=O)=O.[BH4-].[Na+]>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH2:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[S:7][C:6]=2[CH:17]=1

Participants

5

Reactant 3

HCID 31347SulfolaneHCID 4311764Sodium borohydrideHCID 20270218HCID 20270218, compound

Product 1

HCID 13151860HCID 13151860, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10.55 G. 3,11-dibromo-10,11-dihydrodibenzo[b,f]thiepin is suspended in 150 cc. sulfolane and gradually, in portions, 3.5 g. sodium borohydride is added. When the foaming has subsided, water is added and the mixture extracted four times with ether, the combined extracts are washed several times with water, dried and evaporated to dryness, and the residual oil chromatographed on silica gel. On elution with 10% benzene in hexane, 3.31 g. of pure material as a white solid is obtained, m.p. 69°-71° C.

Workup

  1. extractionthe mixture extracted four times with ether
  2. washthe combined extracts are washed several times with water
  3. customdried
  4. customevaporated to dryness
  5. customthe residual oil chromatographed on silica gel
  6. washOn elution with 10% benzene in hexane, 3.31 g
  7. customof pure material as a white solid is obtained

Sources & evidence

ORD record
ord-91d3b4ab4aa943c7aeb26eed61b68c21
Source dataset
uspto-grants-1985_08
Patent number
US04536507

Reaction notes

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