Trifluoroacetic acid → 2-Methoxyphenethyl bromide

HRID 2353617Notes

Reaction equation

HRID 2353617 reaction equation
C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O.[Br:15][CH2:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH3:26])=O.[OH-].[Na+]>C([O-])(O)=O.[Na+]>[Br:15][CH2:16][CH2:17][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH3:26]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 14798Sodium HydroxideHCID 123440Bromomethyl 2-methoxyphenyl ketone

Product 1

HCID 5781992-Methoxyphenethyl bromideYield 69.7%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of triethylsilane (34.9 g, 0.3 mol), TFA (96 mL) and 2-bromo-1-(2-methoxy-phenyl)-ethanone (6.9 g, 30 mmol) is stirred at rt for 30 min before it is poured onto an ice/water mixture (600 mL). The mixture is neutralised by adding 2 N aq. NaOH and sat. aq. NaHCO3 (200 mL), and is extracted with DCM (2×200 mL). The combined organic extracts are dried over Na2SO4, filtered and evaporated. The obtained residue is purified by chromatography on silica gel (TBME:EA 40:1) to give 1-(2-bromo-ethyl)-2-methoxy-benzene (4.50 g) as a colourless liquid. LC: tR=1.00 min.

Workup

  1. extractionis extracted with DCM (2×200 mL)
  2. dry with materialThe combined organic extracts are dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe obtained residue is purified by chromatography on silica gel (TBME:EA 40:1)

Sources & evidence

ORD record
ord-41f79517d29a47a98dde643db3e3fc9e
Source dataset
uspto-grants-2010_07
Patent number
US07750040B2

Reaction notes

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