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4-Bromophenol → (2S)-2-(4-bromophenoxy)propanoic acid, ethyl ester

HRID 379967
Notes
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Reaction equation

HRID 379967 reaction equation
CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:32]([O:37][CH2:38][CH3:39])(=[O:36])[C@@H:33]([CH3:35])[OH:34].[Br:40][C:41]1[CH:46]=[CH:45][C:44](O)=[CH:43][CH:42]=1>O1CCCC1>[Br:40][C:41]1[CH:46]=[CH:45][C:44]([O:34][C@@H:33]([CH3:35])[C:32]([O:37][CH2:38][CH3:39])=[O:36])=[CH:43][CH:42]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 78084-BromophenolHCID 11776TriphenylphosphineHCID 637513ethyl (2R)-2-hydroxypropanoateHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 86756006(2S)-2-(4-bromophenoxy)propanoic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

Prepared according to the method described in Example 1a) from diethylazodicarboxylate (6.7 ml), triphenylphosphine (13.11 g), (R)-(+)-ethyl lactate (5.67 ml) and 4-bromophenol (8.65 g) in dry tetrahydrofuran (125 ml). The residue obtained after work-up was purified by column chromatography over silica eluting with isohexane:dichloromethane (2:3) to give the sub-title compound as an oil (12.2 g).

Workup

  1. customPrepared
  2. customThe residue obtained after work-up
  3. customwas purified by column chromatography over silica eluting with isohexane:dichloromethane (2:3)

Sources & evidence

ORD record
ord-e639739a1c3d4e48abee8a3c6cdade37
Source dataset
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06300352B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes