2-(4-Fluorophenylthio)-6-fluorobenzoic acid → 2-(4-Fluorophenylthio)-6-fluorobenzyl alcohol

HRID 1974756Notes

Reaction equation

HRID 1974756 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]1[CH:13]=[CH:12][C:11]([S:14][C:15]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:16]=2[C:17](O)=[O:18])=[CH:10][CH:9]=1>C(OCC)C.C1COCC1>[F:7][C:8]1[CH:9]=[CH:10][C:11]([S:14][C:15]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:16]=2[CH2:17][OH:18])=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 191022242-(4-Fluorophenylthio)-6-fluorobenzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 545494552-(4-Fluorophenylthio)-6-fluorobenzyl alcohol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

LiAlH4 (0.77 g, 20.4 mmol) is suspended in 30 ml of dry diethyl ether with cooling in an ice bath. 2-(4--fluorophenylthio)-6-fluorobenzoic acid (4.53 g, 17.0 mmol) in 6 ml of diethyl ether and 6 ml of THF is then added and the reaction mixture stirred at room temperature overnight. The reaction mixture is quenched sequentially with 0.8 ml of water, 0.8 ml of 15% NaOH aqueous solution, and 2.4 ml of water. The resulting white precipitate is filtered off and washed thoroughly with diethyl ether. The filtrate and washings are combined and concentrated to afford the subtitle compound.

Workup

  1. temperaturewith cooling in an ice bath
  2. customThe reaction mixture is quenched sequentially with 0.8 ml of water, 0.8 ml of 15% NaOH aqueous solution, and 2.4 ml of water
  3. filtrationThe resulting white precipitate is filtered off
  4. washwashed thoroughly with diethyl ether
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f8dc75b1958c49ffb6f6233a266fab05
Source dataset
uspto-grants-1994_02
Patent number
US05283361

Reaction notes

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