Tetrahydrofuran → 2-Chloro-3,6-difluoro-α-methylbenzenemethanol

HRID 912032Notes

Reaction equation

HRID 912032 reaction equation
[Cl:1][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([F:11])[C:3]=1[CH:4]=[O:5].[CH2:12]1COCC1.C[Mg]Br.[NH4+].[Cl-]>C(OCCCC)CCC.C(OCC)C>[Cl:1][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([F:11])[C:3]=1[CH:4]([OH:5])[CH3:12]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 27735092-Chloro-3,6-difluorobenzaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 211113742-Chloro-3,6-difluoro-α-methylbenzenemethanol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8909Butyl etherSolvent

Procedure

To a dry 18×250 mm test tube, 2-Chloro-3,6-difluorobenzaldehyde (1.00 g, 5.66 mmol) and THF (10.0 mL, 123 mmol) were added. The reaction tube was evacuated and filled with N2 3 times. Methylmagnesium bromide (0.810 g, 6.80 mmol) 1.0 M in butyl ether was added slowly at 0° C. The reaction mixture was stirred at room temperature overnight. 5 mL of sat. aq. NH4Cl was added to quench the reaction at 0° C. Diethyl ether was added and aq. layer was extracted with ether 3 times. The combined organic layers were dried over Na2SO4 and the solvent was removed in vacuo. The material was not further purified and ready for the next step.

Workup

  1. additionwere added
  2. customThe reaction tube was evacuated
  3. additionfilled with N2 3 times
  4. customto quench
  5. customthe reaction at 0° C
  6. extractionaq. layer was extracted with ether 3 times
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. customthe solvent was removed in vacuo
  9. customThe material was not further purified and ready for the next step

Sources & evidence

ORD record
ord-34042af9b0bf4868911e47211ea3ee82
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

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