Tetrahydrofuran → 3-Bromo-2,5-difluoro-alpha-methylbenzenemethanol

HRID 1607182Notes

Reaction equation

HRID 1607182 reaction equation
[Br:1][C:2]1[C:3]([F:11])=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH:5]=[O:6].[CH2:12]1COCC1.C[Mg+].[Br-]>CCOCC>[Br:1][C:2]1[C:3]([F:11])=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH:5]([OH:6])[CH3:12]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 146210213-Bromo-2,5-difluorobenzaldehydeHCID 178418689HCID 178418689, compound

Product 1

HCID 146210223-Bromo-2,5-difluoro-alpha-methylbenzenemethanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred mixture of 13.3 g of 3-bromo-2,5-difluorobenzaldehyde and 300 mL of THF cooled to -35°/-20° under an N2 atmosphere is added 30 mL of 2.85M of MeMgBr in Et2O over 10 minutes. The cooling bath is removed and the mixture stirred 1 hour and finally poured into 1 L of ice/H2O. 10% HCl is added to bring the pH to ~2 and the mixture extracted with 3×200 ml of CH2Cl2. The CH2Cl2 extracts are washed with H2O, saturated NaHCO3, H2O (250 mL each) and stripped to furnish 14.5 g of crude 3-bromo-2,5-difluoro-α-methylbenzyl alcohol. M+1 ions are observed at 236 and 238 in the mass spectrum. The crude material is used directly in the next step.

Workup

  1. temperaturecooled to -35°/-20° under an N2 atmosphere
  2. customThe cooling bath is removed
  3. additionfinally poured into 1 L of ice/H2O
  4. addition10% HCl is added
  5. extractionthe mixture extracted with 3×200 ml of CH2Cl2
  6. washThe CH2Cl2 extracts are washed with H2O, saturated NaHCO3, H2O (250 mL each)

Sources & evidence

ORD record
ord-66acacaa37294dea9887a62028044a39
Source dataset
uspto-grants-1989_09
Patent number
US04863959

Reaction notes

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