D-Phenylalanine → 3-(2-Bromophenyl)propionic acid

HRID 266035

Reaction equation

N([O-])=O.[Na+].N[C@@H:6]([C:14]([OH:16])=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Br-:17].[K+]>S(=O)(=O)(O)O>[CH:12]1[CH:13]=[C:8]([CH2:7][CH2:6][C:14]([OH:16])=[O:15])[C:9]([Br:17])=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium nitrite (10.3 g, 280 mmol) was added to a solution of D-phenylalanine (30.0 g, 181 mmol) and potassium bromide (73.5 g) in sulfuric acid (2.5N, 365 ml) over a period of one hour while maintaining the temperature of the reaction mixture at 0° C. The mixture was stirred for an additional hour at 0° C. and then for one hour at room temperature. The reaction solution was extracted with ether, the ether was back extracted with water, and the ether layer was dried over sodium sulfate. Ether was removed in vacuo, and distillation of the oily residue afforded 25.7 g of (R)-2-bromo-3-benzenepropanoic acid; b.p. 141° C. (0.55 mm of Hg); [α]D =+14.5° (c=2.4, chloroform).

Workup

extractionThe reaction solution was extracted with ether
extractionthe ether was back extracted with water
dry with materialthe ether layer was dried over sodium sulfate
customEther was removed in vacuo, and distillation of the oily residue

Sources & evidence

ORD record: ord-a9c7661f29dc43ce8ac5440c0f49aeec
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05650408

Linked notes

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