Hydrochloric Acid → 2-(4-Fluorophenyl)ethane-1-thiol

HRID 709441Notes

Reaction equation

HRID 709441 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][S:10]C(=O)C)=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.Cl>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][SH:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21226445Aluminium lithium hydride2×HCID 23577239Thioacetic acid S-[2-(4-fluoro-phenyl)-ethyl]ester

Product 1

HCID 186687292-(4-Fluorophenyl)ethane-1-thiol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Thioacetic acid S-[2-(4-fluoro-phenyl)-ethyl]ester (9.9 g, 50 mmol) was dissolved in anhydrous THF (300 mL) and LiAlH4 (7.5 g, 200 mmol) was added in several small portions. After the addition was completed the mixture was stirred for 2 h at room temperature then cooled down to 0° C. and excess LiAlH4 was hydrolyzed by the addition of H2O (10 mL) and aq. HCl (2N, 200 mL). The resulting clear solution was extracted with EtOAc (3×200 mL) and the combined organic layers were dried (MgSO4) and evaporated under reduced pressure. The unpleasant smelling crude product (8.17 g, 104%) was carried on into the next step as obtained. 1H NMR (400 MHz, CDCl3): δ 7.17 (dd, 2H), 7.02 (t, 2H), 2.89 (t, 2H), 2.78 (dd, 2H), 1.38 (t, 1H).

Workup

  1. additionAfter the addition
  2. temperaturethen cooled down to 0° C.
  3. extractionThe resulting clear solution was extracted with EtOAc (3×200 mL)
  4. dry with materialthe combined organic layers were dried (MgSO4)
  5. customevaporated under reduced pressure
  6. customas obtained

Sources & evidence

ORD record
ord-f9b2b16f1a7448f6b9bd4a02025e2f64
Source dataset
uspto-grants-2015_11
Patent number
US09181181B2

Reaction notes

Loading…