Dimethyl Sulfide → (S)-1-(2,6-dichloro-3-fluorophenyl)ethanol

HRID 587115Notes

Reaction equation

HRID 587115 reaction equation
B1(C)OC(C2C=CC=CC=2)(C2C=CC=CC=2)[C@@H]2N1CCC2.S(C)C.ClCCl.[Cl:28][C:29]1[C:34]([F:35])=[CH:33][CH:32]=[C:31]([Cl:36])[C:30]=1[C:37](=[O:39])[CH3:38]>Cl.CO>[Cl:28][C:29]1[C:34]([F:35])=[CH:33][CH:32]=[C:31]([Cl:36])[C:30]=1[C@@H:37]([OH:39])[CH3:38]

Participants

7

Reactant 4

HCID 1068Dimethyl SulfideHCID 6344DichloromethaneHCID 27339821-(2,6-Dichloro-3-fluorophenyl)ethanoneHCID 9838490(R)-2-Methyl-CBS-oxazaborolidine

Product 1

HCID 11557536(S)-1-(2,6-dichloro-3-fluorophenyl)ethanol

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

To (R)-2-methyl-CBS-oxazaborolidine (Aldrich or Callery Chemical Co, 1M in toluene, 1 eq.) at −45° C. is added BH3. Me2S (1.06 eq.). To the previous solution is added at −30° C. a 1M dichloromethane solution of 1-(2,6-dichloro-3-fluorophenyl)ethanone. After completion of the reaction, excess MeOH is added followed by IN HCl. After warming up to room temperature, the resulting mixture is filtered through a pad of celite and silica gel and washed with 30% EtOAc in hexane. The solvent is removed under reduced pressure and the resulting oil is purified by flash chromatography (20% EtOAc in hexane) to afford (S)-1-(2,6-dichloro-3-fluorophenyl)ethanol (optically enriched).

Workup

  1. additionis added
  2. filtrationthe resulting mixture is filtered through a pad of celite and silica gel
  3. washwashed with 30% EtOAc in hexane
  4. customThe solvent is removed under reduced pressure
  5. customthe resulting oil is purified by flash chromatography (20% EtOAc in hexane)

Sources & evidence

ORD record
ord-1ad501c69fca4463955e913e872b85ab
Source dataset
uspto-grants-2016_01
Patent number
US09226923B2

Reaction notes

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