Bromobenzene → HCID 67745319, compound

HRID 375474Notes

Reaction equation

HRID 375474 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]2[C:13](=[O:17])[CH2:14][CH2:15][S:16][CH:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]1([Mg]Br)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.BrC1C=CC=CC=1.[Mg].[Cl-].[NH4+]>C(OCC)C>[OH:17][C:13]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:11]2[CH:10]([CH2:9][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:12]2)[S:16][CH2:15][CH2:14]1

Participants

7

Reactant 5

HCID 7961BromobenzeneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 67745323HCID 67745323, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 67745319HCID 67745319, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A solution of 21.15 g of (4aRS,7aSR)6-benzyl-4-oxoperhydrothiopyrano[2,3-c]pyrrole in 150 cm3 of anhydrous ethyl ether are added over 30 minutes to a solution of phenylmagnesium bromide prepared from 19.8 cm3 of bromobenzene and 4.52 g of dry magnesium in 120 cm3 of anhydrous ethyl ether. The reaction mixture is stirred at the reflux temperature for 3 hours, and then for 20 hours at 20° C. The mixture, to which 200 cm3 of ethyl ether has been added, is stirred with 600 cm3 of a saturated aqueous solution of ammonium chloride. The aqueous phase is extracted with 200 cm3 of ethyl ether, the two pooled etherial extracts are washed twice with 300 cm3 of a saturated aqueous solution of sodium chloride and then dried over magnesium sulphate and concentrated to dryness under reduced pressure (5.4 kPa) at 35° C. 12.2 g of (4RS,4aSR,7aRS)-4-hydroxy-4-phenyl6-benzylperhydrothiopyrano[2,3-c]pyrrole are obtained in the form of a white solid; melting point 137° C.

Workup

  1. waitfor 20 hours at 20° C
  2. extractionThe aqueous phase is extracted with 200 cm3 of ethyl ether
  3. washthe two pooled etherial extracts are washed twice with 300 cm3 of a saturated aqueous solution of sodium chloride
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated to dryness under reduced pressure (5.4 kPa) at 35° C

Sources & evidence

ORD record
ord-e34715e7fd2a401eae48bb89563f9e12
Source dataset
uspto-grants-1996_01
Patent number
US05484942

Reaction notes

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