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Hydrochloric Acid → m-Phenoxybenzyl 2-bromo-3-methyl-3-butenoate

HRID 648251
Notes
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Reaction equation

HRID 648251 reaction equation
C([N-]C1CCCCC1)(C)C.[Li+].[CH3:12][C:13]([CH3:32])=[CH:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:20]=1)=[O:16].[Br:33]Br.Cl>C1COCC1.CCOCC.CN(P(N(C)C)(N(C)C)=O)C>[Br:33][CH:14]([C:13]([CH3:32])=[CH2:12])[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:20]=1)=[O:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 313Hydrochloric Acid2×HCID 24408BromineHCID 10877271Lithium cyclohexylisopropylamideHCID 20482725(3-Phenoxyphenyl)methyl 3-methylbut-2-enoate

Product 1

HCID 20482806m-Phenoxybenzyl 2-bromo-3-methyl-3-butenoate

Reagents, catalysts & solvents 3

HCID 3283
Diethyl Ether
Solvent
HCID 8028TetrahydrofuranSolvent3×
HCID 12679HexamethylphosphoramideSolvent

Procedure

A 100 ml flask is flushed with nitrogen and to it is added 25 ml of a 1 M THF solution of lithium N-isopropylcyclohexylamide (0.025 mole) followed by HMPT (5 ml). The flask is cooled to -78° and 7.1 g (0.025 mole) of m-phenoxybenzyl 3-methyl-2-butenoate in THF (25 ml) is added dropwise over 5 minutes. After the addition the mixture is stirred at -20° for 1 hour. This cold solution is then added dropwise to 1.1 equivalent of bromine in THF at -78°. After a further 1 hour at -78°, 5 ml of concentrated hydrochloric acid is added and the mixture allowed to come to RT and poured into ether plus cold aqueous hydrochloric acid. The ether layer is washed with water and brine and dried over calcium sulfate. Removal of the solvent gives m-phenoxybenzyl 2-bromo-3-methyl-3-butenoate, which is reacted with p-methylaniline by the process of Example 5 to give m-phenoxybenzyl ester of 2-(p-methylphenylamino)-3-methyl-3-butenoate.

Workup

  1. customA 100 ml flask is flushed with nitrogen and to it
  2. temperatureThe flask is cooled to -78°
  3. additionAfter the addition the mixture
  4. waitAfter a further 1 hour at -78°
  5. customto come to RT
  6. washThe ether layer is washed with water and brine
  7. dry with materialdried over calcium sulfate
  8. customRemoval of the solvent

Sources & evidence

ORD record
ord-b800be58ef504390999398529cc10f76
Source dataset
uspto-grants-1983_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04411912

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes