Bromoacetyl bromide → HCID 87076249, compound

HRID 1627743Notes

Reaction equation

HRID 1627743 reaction equation
[C:1]([O:11][CH3:12])(=[O:10])[C@@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].[Br:13][CH2:14][C:15](Br)=[O:16]>>[Br:13][CH2:14][C:15]([O:3][C@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:1]([O:11][CH3:12])=[O:10])=[O:16]

Participants

3

Reactant 2

HCID 61147Bromoacetyl bromideHCID 2724623(R)-(-)-Methyl mandelate

Product 1

HCID 87076249HCID 87076249, compoundYield 88%

Procedure

To methyl (R)-mandelate (8.3 g, 150 mmol), and neutral alumina [e.g. Aldrich type WN-3] (17 g, 167 mmol) cooled with an ice-bath was added bromoacetyl bromide (44 mL, 500 mmol). The ice bath was removed and after 1 h standing at RT, the reaction mixture was poured onto solid NaHCO3 (117 g) in a glass filter funnel, with a cotton wool plug (effervescence). After standing overnight, the solid was washed with toluene until 200 ml of filtrate had been collected. The volatiles were removed via rotary evaporation to yield a crude product in 88% yield. This crude product was sufficiently pure to carry through to the next step.

Workup

  1. customThe ice bath was removed and after 1 h
  2. customstanding at RT
  3. additionthe reaction mixture was poured onto solid NaHCO3 (117 g) in a glass
  4. filtrationfilter funnel
  5. washthe solid was washed with toluene until 200 ml of filtrate
  6. customhad been collected
  7. customThe volatiles were removed via rotary evaporation

Sources & evidence

ORD record
ord-6ee71f434006449fafab1f6cd5e40636
Source dataset
uspto-grants-2014_07
Patent number
US08785655B2

Reaction notes

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