1-Bromo-2-(diethoxymethyl)benzene → [2-(Diethoxymethyl)-phenyl](4-chloro-2-fluorophenyl)-methanone

HRID 1422130Notes

Reaction equation

HRID 1422130 reaction equation
[CH2:1]([O:3][CH:4]([O:12][CH2:13][CH3:14])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1Br)[CH3:2].C([Li])CCC.CON(C)[C:23](=[O:32])[C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=1[F:31]>C(OCC)C.CCCCCC>[CH2:1]([O:3][CH:4]([O:12][CH2:13][CH3:14])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:23]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=1[F:31])=[O:32])[CH3:2]

Participants

6

Reactant 3

HCID 34827781-Bromo-2-(diethoxymethyl)benzeneHCID 222258304-chloro-2-fluoro-N-methoxy-N-methylbenzamideHCID 178418339Butyllithium

Product 1

HCID 18357490[2-(Diethoxymethyl)-phenyl](4-chloro-2-fluorophenyl)-methanoneYield 142.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

A stirred solution of 10.6 g of 2-bromobenzaldehyde diethyl acetal in 100 ml of diethyl ether was cooled to -40° C. To this cold solution was added rapidly 46 ml of a 1.2 M solution of butyllithium in hexane. The solution was warmed to 0° C. over 30 min. The solution was cooled down to -40° C. and a solution of 11.9 g of N-Methoxy-N-methyl-4-chloro-2-fluorobenzamide in 100 ml of diethyl ether added by cannular. The solution was warmed to 0° C. and stirred for 0.75 h then quenched by the addition of 100 ml of water and 200 ml of ether added. The organic layer was separated and the aqueous layer was extracted with 200 ml of ether. The combined organic layers were dried over sodium sulfate and evaporated to yield 19.6 g of crude [2-(diethoxymethyl)-phenyl](4-chloro-2-fluorophenyl)-methanone as a gum, GC-M.S. (E.I.) (M/Z) 336 [M]+.

Workup

  1. temperatureThe solution was cooled down to -40° C.
  2. temperatureThe solution was warmed to 0° C.
  3. customthen quenched by the addition of 100 ml of water and 200 ml of ether
  4. additionadded
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with 200 ml of ether
  7. dry with materialThe combined organic layers were dried over sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-55a0edacc357466bae6f518df9977ead
Source dataset
uspto-grants-2000_06
Patent number
US06080773

Reaction notes

Loading…