HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → 4-Bromo-2,5-difluorobenzaldehyde
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | 1,4-Dibromo-2,5-difluorobenzene | HCID 67596 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-Bromo-2,5-difluorobenzaldehyde | HCID 22489081 | 74.2% |
Reaction Conditions
| Temperature | -40 °C |
|---|
Reaction Steps
To 1,4-dibromo-2,5-difluorobenzene (10.28 g, 37.81 mmol) in tetrahydrofuran (80 mL) at −40° C. was isopropylmagnesium chloride lithium chloride complex (29.1 mL, 37.81 mmol) added dropwise. After 1 h at −40° C. was N,N-dimethylformamide (58 mL, 756 mmol) added and the mixture was stirred for 30 minutes at −40° C. NH4Cl (2M, aq, 100 mL) was added and the mixture was extracted with ethyl acetate. The organic phase was dried with MgSO4 and concentrated to give 4-bromo-2,5-difluorobenzaldehyde (6.20 g, 74%) as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08178529B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-4e4092541b69455e932f50db8737cdd0 |
| Source note | uspto-grants-2012_05 |