Cesium carbonate → 3-Bromo-4-(difluoromethoxy)benzaldehyde

HRID 1632111Notes

Reaction equation

HRID 1632111 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:18]([F:23])([F:22])C([O-])=O.[Na+]>>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH:18]([F:23])[F:22])[CH:5]=[O:6]

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 763083-Bromo-4-hydroxybenzaldehydeHCID 2734985Sodium chlorodifluoroacetate

Product 1

HCID 577037453-Bromo-4-(difluoromethoxy)benzaldehyde

Conditions

Temperature
65 °C

Procedure

A suspension of 3-bromo-4-hydroxy-benzaldehyde (4.97 mmol; 1.0 eq.), cesium carbonate (7.46 mmol; 1.5 eq.) and sodium chlorodifluoroacetate was stirred at 65° C. for 5.5 h. The mixture was partitioned with ethyl acetate and water, and the aqueous portion extracted with diethyl ether. The combined extracts were washed with successive portions of water and brine, dried over magnesium sulfate, filtered and concentrated to afford the title compound, I-286, as a yellow oil. 1H NMR (400 MHz, DMSO-d6): 7.49 (t, J=72.4 Hz, 3H), 7.54 (d, J=8.4 Hz, 1H), 8.00 (dd, J=8.4, 2.0 Hz, 1H), 8.26 (d, J=2.0 Hz, 1H), 9.96 (s, 1H) ppm.

Workup

  1. customThe mixture was partitioned with ethyl acetate and water
  2. extractionthe aqueous portion extracted with diethyl ether
  3. washThe combined extracts were washed with successive portions of water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d0900d4bb739414da14a7c89c64cecf6
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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