2-Fluoroethanol → Benzene, 1-bromo-4-(2-fluoroethoxy)-2-methyl-

HRID 1012607Notes

Reaction equation

HRID 1012607 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].[F:10][CH2:11][CH2:12]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.CCOC(C)=O.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:12][CH2:11][F:10])=[CH:4][C:3]=1[CH3:9]

Participants

7

Reactant 4

HCID 97372-FluoroethanolHCID 11776TriphenylphosphineHCID 728574-Bromo-m-cresolHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 71742682Benzene, 1-bromo-4-(2-fluoroethoxy)-2-methyl-

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22728543Water ethylacetateSolvent

Procedure

A solution of 4-bromo-3-methyl-phenol (3.74 g, 20 mmol), 2-fluoro-ethanol (2.29 mL, 22 mmol), and triphenylphosphine (5.77 g, 22 mmol) in dry THF (15 mL) was cooled to 0° C. under stirring. Diethyl azodicarboxylate (40% in toluene, 10 mL, 22 mmol) was added and the reaction mixture was allowed to come to RT overnight. After 18 h at RT the reaction mixture was poured into a mixture of EtOAc/water. The aqueous phase was extracted with more EtOAc. The organic phases were combined, dried (MgSO4), filtered, and concentrated in vacuo to afford the crude product. The crude product was purified by chromatography eluting with DCM/petroleum ether 1:6 to afford the title compound as colourless oil.

Workup

  1. extractionThe aqueous phase was extracted with more EtOAc
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto afford the crude product
  6. customThe crude product was purified by chromatography
  7. washeluting with DCM/petroleum ether 1:6

Sources & evidence

ORD record
ord-a88a19ad1b9a43968650b78c747f3f8a
Source dataset
uspto-grants-2011_07
Patent number
US07977387B2

Reaction notes

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