Sodium borohydride → HCID 13059709, compound

HRID 223170Notes

Reaction equation

HRID 223170 reaction equation
[Br:1][CH:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][C:7]([Cl:13])=[CH:8][CH:9]=2)[S:4][CH2:3]1.[BH4-].[Na+]>CO>[Br:1][CH:2]1[CH:11]([OH:12])[C:10]2[C:5](=[CH:6][C:7]([Cl:13])=[CH:8][CH:9]=2)[S:4][CH2:3]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 13059708HCID 13059708, compound

Product 1

HCID 13059709HCID 13059709, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0.5 °C

Procedure

Suspend 3-bromo-7-chlorothiochroman-4-one (59.6 gms., 215 mmols) in methanol (500 ml.), cool to 0.5° C., and with stirring add sodium borohydride (8.18 gms., 215 mmols) in three portions. Continue stirring the reaction mixture at room temperature for three hours, then pour into ice water (4 liters) and extract with chloroform (2 liters). Dry the chloroform solution over anhydrous magnesium sulfate, filter and evaporate in vacuo to a residue. Triturate the residue with chloroform/hexane to give 3-bromo-7-chlorothiochroman-4-ol, m.p. 141°-142° C.

Workup

  1. stirringContinue stirring the reaction mixture at room temperature for three hours
  2. extractionextract with chloroform (2 liters)
  3. dry with materialDry the chloroform solution over anhydrous magnesium sulfate
  4. filtrationfilter
  5. customevaporate in vacuo to a residue
  6. customTriturate the residue with chloroform/hexane

Sources & evidence

ORD record
ord-e908487b3e8a4e4fb1694bc7936ec7ba
Source dataset
uspto-grants-1982_10
Patent number
US04352808

Reaction notes

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