5-Bromo-2-fluorobenzaldehyde → HCID 53854056, compound

HRID 2395602Notes

Reaction equation

HRID 2395602 reaction equation
[CH2:1]([Li])[CH2:2]CC.[Br:6][C:7]1[CH:8]=[CH:9][C:10]([F:15])=[C:11]([CH:14]=1)[CH:12]=O>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.CCCCCC.C1COCC1>[Br:6][C:7]1[CH:8]=[CH:9][C:10]([F:15])=[C:11]([CH:12]=[CH:1][CH3:2])[CH:14]=1

Participants

6

Reactant 2

HCID 7363275-Bromo-2-fluorobenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 53854056HCID 53854056, compound

Reagents, catalysts & solvents 3

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)CatalystHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-50 °C

Procedure

A mixture of 16.5 g (0.044 mol) of ethyltriphenylphosphonium bromide and 387 ml of anhydrous THF is cooled to -50° C. under a nitrogen atmosphere. 27.8 ml (0.044 mol) of a 1.6M solution of n-butyllithium in hexane are added dropwise. The mixture is allowed to return to 0° and is stirred for 1 h at 0° C. The mixture is cooled to -30° C. and a solution of 8.8 g (0.0433 mol) of 5-bromo-2-fluorobenzaldehyde in 43 ml of anhydrous THF is added dropwise. The mixture is stirred overnight at room temperature and then for 2 h at 40° C. Filtration is carried out and the filtrate is evaporated under vacuum.

Workup

  1. customto return to 0°
  2. temperatureThe mixture is cooled to -30° C.
  3. stirringThe mixture is stirred overnight at room temperature
  4. waitfor 2 h at 40° C
  5. filtrationFiltration
  6. customthe filtrate is evaporated under vacuum

Sources & evidence

ORD record
ord-c4a907a7ebc3400ebd05676b45ad61b2
Source dataset
uspto-grants-1996_02
Patent number
US05489592

Reaction notes

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