4-Amino-3-bromo-2,5-difluorobenzaldehyde → 4-Amino-3-bromo-2,5-difluoro-alpha-methylbenzyl alcohol

HRID 1607188Notes

Reaction equation

HRID 1607188 reaction equation
[NH2:1][C:2]1[C:9]([F:10])=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([F:11])[C:3]=1[Br:12].[CH3:13][Mg+].[Br-]>C1COCC1>[NH2:1][C:2]1[C:9]([F:10])=[CH:8][C:5]([CH:6]([OH:7])[CH3:13])=[C:4]([F:11])[C:3]=1[Br:12]

Participants

4

Reactant 2

HCID 146210204-Amino-3-bromo-2,5-difluorobenzaldehydeHCID 178418689HCID 178418689, compound2×

Product 1

HCID 146210344-Amino-3-bromo-2,5-difluoro-alpha-methylbenzyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 20 g of 4-amino-3-bromo-2,5-difluorobenzaldehyde and 400 mL of THF under an N2 atmosphere and cooled in ice is added 60 mL of an 2.85M ethereal solution of MeMgBr. The addition is carried out over 15 minutes at a temperature of 10°-16° C. 80 minutes later another 40 mL of MeMgBr is added and the ice bath is removed. 2 hours later the mixture is poured into 1 L of ice/H2O and 10% HCl is added to pH 4. The mixture is extracted with 3×300 mL of CH2Cl2. The extracts are washed with 2×150 mL of H2O, dried with Na2SO4 and stripped in vacuo to give 21.76 g of crude 4-amino-3-bromo-2,5-difluoro-α-methylbenzyl alcohol with M+1 ions at 252 and 254 in the mass spectrum.

Workup

  1. additionThe addition
  2. customthe ice bath is removed
  3. addition2 hours later the mixture is poured into 1 L of ice/H2O and 10% HCl
  4. additionis added to pH 4
  5. extractionThe mixture is extracted with 3×300 mL of CH2Cl2
  6. washThe extracts are washed with 2×150 mL of H2O
  7. dry with materialdried with Na2SO4

Sources & evidence

ORD record
ord-492ab92b38d348feba2680f075255992
Source dataset
uspto-grants-1989_09
Patent number
US04863959

Reaction notes

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