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Water → 3-[2-(2-Bromo-5-fluoro-phenoxymethyl)-phenyl]-acrylic acid ethyl ester

HRID 244340
Notes
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Reaction equation

HRID 244340 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1I.C([O-])(=O)C.[Na+].[C:23]([O:27][CH2:28][CH3:29])(=[O:26])[CH:24]=[CH2:25].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN1CCCC1=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.C(OC)(C)(C)C>[CH2:28]([O:27][C:23](=[O:26])[CH:24]=[CH:25][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[CH2:10][O:9][C:3]1[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=1[Br:1])[CH3:29]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

10

Reactant 4

HCID 962WaterHCID 8821Ethyl AcrylateHCID 517045Sodium AcetateHCID 585644251-Bromo-4-fluoro-2-(2-iodo-benzyloxy)-benzene

Product 1

HCID 671334433-[2-(2-Bromo-5-fluoro-phenoxymethyl)-phenyl]-acrylic acid ethyl esterYield 95%

Reagents, catalysts & solvents 5

HCID 74236
Tetrabutylammonium Bromide
Catalyst
HCID 167845palladium(II) acetateCatalyst
HCID 8857Ethyl AcetateSolvent
HCID 13387N-methyl-2-pyrrolidoneSolvent2×
HCID 15413tert-Butyl methyl etherSolvent

Procedure

To a mixture of 1-bromo-4-fluoro-2-(2-iodo-benzyloxy)-benzene (117.4 g, 0.29 mol), sodium acetate (36.1 g, 0.44 mol), tetra-n-butylammonium bromide (90.3 g, 0.29 mol), palladium (II) acetate (1.8 g, 8 mmol, 3 mol %), and N-methylpyrrolidinone (900 mL) at 55-60° C., add dropwise a solution of ethyl acrylate (34.3 mL, 0.32 mol) in N-methylpyrrolidinone (200 mL). Cool the reaction mixture to room temperature and treat with water (2 L) and methyl tert-butyl ether (2 L). Pass the reaction through diatomaceous earth, add ethyl acetate (1 L), separate the layers, and wash with water (2 L). Dry the organic portion over anhydrous sodium sulfate, filter, and concentrate. Suspend the resulting solid in hexanes (1 L), refrigerate for 2 h, filter, and wash with cold hexanes (500 mL). Dry in a vacuum oven (50° C./20 mm Hg) to obtain the title compound as a pale yellow solid (104.4 g, 95%). LC-MS m/z 381.0 [M+H]+.

Workup

  1. customPass the reaction through diatomaceous earth
  2. customseparate the layers
  3. washwash with water (2 L)
  4. dry with materialDry the organic portion over anhydrous sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate
  7. filtrationfilter
  8. washwash with cold hexanes (500 mL)
  9. customDry in a vacuum oven (50° C./20 mm Hg)

Sources & evidence

ORD record
ord-4e33039bc6054fbf846988590793f18d
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08658638B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes