Lithium borohydride → [5-(3-Bromophenylsulphanylmethyl)-2-hydroxymethylphenyl]methanol

HRID 2307549Notes

Reaction equation

HRID 2307549 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:8][CH2:9][C:10]2[CH:11]=[C:12]([C:20](OC)=[O:21])[C:13](=[CH:18][CH:19]=2)[C:14](OC)=[O:15])[CH:5]=[CH:6][CH:7]=1.[BH4-].[Li+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([S:8][CH2:9][C:10]2[CH:19]=[CH:18][C:13]([CH2:14][OH:15])=[C:12]([CH2:20][OH:21])[CH:11]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 22606944Dimethyl 4-(3-bromophenylsulphanylmethyl)phthalate

Product 1

HCID 22606907[5-(3-Bromophenylsulphanylmethyl)-2-hydroxymethylphenyl]methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dimethyl 4-(3-bromophenylsulphanylmethyl)phthalate (10 g, 26 mmol) is dissolved in 120 mL of anhydrous THF. 2.2 g of lithium borohydride (100 mmol) are then added slowly, after which the reaction medium is refluxed for 12 h. After cooling and treatment with saturated ammonium chloride solution, the reaction medium is extracted with ethyl acetate. The organic phases are combined, dried and concentrated under reduced pressure. The residue is purified by chromatography on a column of silica, to give a colourless oil (7.8 g, Y=89%).

Workup

  1. temperatureafter which the reaction medium is refluxed for 12 h
  2. temperatureAfter cooling
  3. extractiontreatment with saturated ammonium chloride solution, the reaction medium is extracted with ethyl acetate
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by chromatography on a column of silica
  7. customto give a colourless oil (7.8 g, Y=89%)

Sources & evidence

ORD record
ord-c5ff1e6233414a4fa92a1d072ca923e8
Source dataset
uspto-grants-2004_12
Patent number
US06831106B1

Reaction notes

Loading…