Water → 36099-25-9

HRID 1405414Notes

Reaction equation

HRID 1405414 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1)=[O:4].[BH4-].[Na+].C([O-])([O-])=O.[K+].[K+].O>CO>[O:4]1[CH2:2][CH:3]1[C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 4311764Sodium borohydrideHCID 13612771Methyl 4-(2-bromoacetyl)benzoate

Product 1

HCID 1479571436099-25-9Yield 90.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 4-(2-bromoacetyl)benzoate (0.59 g, 2.3 mmol) in MeOH (6 mL) at 0° C. was added NaBH4 (92 mg, 2.4 mmol) in portions. The cooling bath was removed and the mixture was stirred at room temperature for 1 h. K2CO3 (317 mg, 2.30 mmol) was added and the mixture was stirred at room temperature for 72 h. The mixture was poured into water and was extracted with Et2O (3×). The organics were combined, washed with water, brine, dried (MgSO4) and evaporated to dryness to give methyl 4-(oxiran-2-yl)benzoate (370 mg, 90%) as a white solid. ESI-MS m/z calc. 178.2, found 179.1 (M+1)+; Retention time: 1.14 minutes (3 min run).

Workup

  1. customThe cooling bath was removed
  2. stirringthe mixture was stirred at room temperature for 72 h
  3. extractionwas extracted with Et2O (3×)
  4. washwashed with water, brine
  5. dry with materialdried (MgSO4)
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-e5eb848a2be347db8a1c8e1da66d7ad0
Source dataset
uspto-grants-2014_12
Patent number
US08916565B2

Reaction notes

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