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Boron trifluoride etherate → Tert-butyl 2-(3-bromophenyl)acetate

HRID 1369052
Notes
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Reaction equation

HRID 1369052 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[C:12](NC(=O)C(Cl)(Cl)Cl)([CH3:15])([CH3:14])[CH3:13].B(F)(F)F.CCOCC.C(=O)(O)[O-].[Na+]>C1CCCCC1.C(Cl)Cl>[C:12]([O:10][C:9](=[O:11])[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)([CH3:15])([CH3:14])[CH3:13]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8000Boron trifluoride etherateHCID 74653(3-Bromophenyl)acetic acidHCID 304045N-tert-butyl-2,2,2-trichloroacetamideHCID 516892Sodium Bicarbonate

Product 1

HCID 53936336Tert-butyl 2-(3-bromophenyl)acetateYield 72.3%

Reagents, catalysts & solvents 2

HCID 6344
Dichloromethane
Solvent
HCID 8078CyclohexaneSolvent

Procedure

To a solution of 3-bromo-phenyl-acetic acid (10 gm, 46.5 mmol) and methylene chloride (47 mL) was added a solution of t-butyl-2,2,2-trichloroacetamidate (20.3 g, 93.0 mmol) and cyclohexane (186 mL) followed by borontrifluoride etherate (0.93 mL, 7.3 mmol). After stirring overnight, solid sodium bicarbonate was added and the reaction then filtered through a pad of silica gel utilizing methylene chloride as solvent. Concentration gave 9.11 g (72%) of a colorless oil.

Workup

  1. customthe reaction
  2. filtrationthen filtered through a pad of silica gel
  3. concentrationConcentration

Sources & evidence

ORD record
ord-cca7140ce1db4a45bb5514cb2f394cec
Source dataset
uspto-grants-2003_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06576632B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes