Hydrogen Bromide → (-)-alpha-Amino-3-(bromomethyl)-4-hydroxybenzeneacetic acid hydrobromide

HRID 903820Notes

Reaction equation

HRID 903820 reaction equation
[NH2:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].[BrH:13].[CH2:14]=O>>[BrH:13].[NH2:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([CH2:14][Br:13])[CH:7]=1)[C:3]([OH:5])=[O:4]

Participants

4

Reactant 3

HCID 260Hydrogen Bromide2×HCID 712FormaldehydeHCID 921434-Hydroxyphenylglycine

Product 1

HCID 70576814(-)-alpha-Amino-3-(bromomethyl)-4-hydroxybenzeneacetic acid hydrobromide

Procedure

To a solution of (-)-α-amino-4-hydroxybenzeneacetic acid (0.6 mole) in a minimum amount of concentrated hydrobromic acid at 35°-40° C. is added 50 ml of aqueous formaldehyde (35-37%) (0.6 mole). The addition of hydrogen bromide gas is begun. After 5-10 minutes, a solid begins to precipitate. Stirring is continued for 30 minutes. The title compound is collected and washed with ether and acetone.

Workup

  1. customto precipitate
  2. waitis continued for 30 minutes
  3. customThe title compound is collected
  4. washwashed with ether and acetone

Sources & evidence

ORD record
ord-948be644b27e4949a130b7349a708db0
Source dataset
uspto-grants-1980_10
Patent number
US04229363

Reaction notes

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