3,5-Dichlorobenzylic alcohol → HCID 66764611, compound

HRID 402837Notes

Reaction equation

HRID 402837 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8](O)=[O:9])[CH:5]=[C:4]([Cl:11])[C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1.ClC1C=C(C=C(Cl)C=1)CO>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[C:4]([Cl:11])[C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 432363,5-Dichlorobenzylic alcoholHCID 667649802,6-Dichloro-4′-fluoro[1,1′-biphenyl]-4-carboxylic acid

Product 1

HCID 66764611HCID 66764611, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2,6-dichloro-4′-fluorobiphenyl-4-carboxylic acid (350 mg, 1.155 mmol) in THF (5 mL) was added 2M borane-methyl sulfide complex in THF (0.35 mL, 0.70 mmol) at room temperature. After 20 hours, the reaction was quenched with 2M HCl and water and was extracted twice with ethyl acetate. The organic layers were washed with brine containing some aqueous sodium bicarbonate, dried over sodium sulfate, combined and concentrated. The residue was purified on silica gel (COMBI FLASH 12 gm column, 100% DCM, then a gradient of 2-10% ethyl acetate/DCM) to give a single main band by TLC (65 mg) containing a 1:1 mixture of title intermediate and 3,5-dichlorobenzyl alcohol from the Step 1 bi-product impurity. The mixture was used directly in Step 3.

Workup

  1. customthe reaction was quenched with 2M HCl and water
  2. extractionwas extracted twice with ethyl acetate
  3. washThe organic layers were washed with brine containing some aqueous sodium bicarbonate
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel (COMBI FLASH 12 gm column, 100% DCM
  7. customa gradient of 2-10% ethyl acetate/DCM) to give a single main band by TLC (65 mg)
  8. additioncontaining

Sources & evidence

ORD record
ord-43b898746b374d3d9e1bf52a210b87fc
Source dataset
uspto-grants-2014_06
Patent number
US08742110B2

Reaction notes

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