Acetic Acid → HCID 57565989, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[F:9].C(NC(C)C)(C)C.[Li].CN(C)[CH:20]=[O:21].C(O)(=O)C>O1CCCC1.O>[F:9][C:3]1[C:2]([F:1])=[CH:7][CH:6]=[C:5]([CH3:8])[C:4]=1[CH:20]=[O:21]Participants
7
Conditions
- Temperature
- -78 °C
Procedure
To a solution of 1,2-difluoro-4-methyl-benzene (5.0 g, 39 mmol) in tetrahydrofuran (200 mL) at −78° C. was added lithium diisopropyl amine (24 mL, 1.8 M in THF, 43 mmol) dropwise during a period of 15 mins. The mixture was stirred at −78° C. for another 20 min. Then N,N-dimethyl-formamide (3.6 mL, 47 mmol) was added in one portion. The mixture was stirred at −78° C. for 10 min, then quenched with acetic acid (9.4 g, 1.56 mmol) and followed by the addition of water (37.6 mL). The mixture was partitioned between ethyl acetate and water. The organic layer was separated, concentrated. The residue was purified by chromatography (EtOAc:hexanes=1:1) to give 2,3-difluoro-6-methyl-benzaldehyde as colorless oil (Yield: 3.5 g, 57.5%).
Workup
- stirringThe mixture was stirred at −78° C. for 10 min
- customThe mixture was partitioned between ethyl acetate and water
- customThe organic layer was separated
- concentrationconcentrated
- customThe residue was purified by chromatography (EtOAc:hexanes=1:1)
Sources & evidence
- ORD record
- ord-c5e03d5665634ecda5cd2e5561acafe7
- Source dataset
- uspto-grants-2009_02
- Patent number
- US07495007B2
Reaction notes
Loading…