N-bromobutanimide → HCID 58415268, compound

HRID 2075188Notes

Reaction equation

HRID 2075188 reaction equation
[Br:1]N1C(=O)CCC1=O.Br[C:10]1[CH:15]=[CH:14][C:13]([CH:16]([O:20]CC)OCC)=[CH:12][C:11]=1[F:23].C1C[O:27][CH2:26][CH2:25]1.O>>[Br:1][CH2:25][C:26]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]=[O:20])=[CH:12][C:11]=1[F:23])=[O:27]

Participants

4

Reactant 3

HCID 67184N-bromobutanimideHCID 21881883Oxolane--water (1/1)HCID 59651817HCID 59651817, compound

Product 1

HCID 58415268HCID 58415268, compound

Conditions

Temperature
25 °C

Procedure

N-Bromosuccinimide (505 mg, 2837 μmol) was added in one portion to a solution of 1-bromo-4-(diethoxymethyl)-2-fluorobenzene (551 mg, 2837 μmol) in 3:1 THF-H2O (6.0 mL) at 25° C., and the resulting solution was stirred at 25° C. for 10 min. The solution was partitioned between EtOAc (50 mL) and brine (8 mL). The organic layer was separated, dried over sodium sulfate, and concentrated in vacuo. Chromatographic purification of the residue (ISCO, 4 g, 0-100% EtOAc/hexanes) furnished 4-(2-bromoacetyl)-3-fluorobenzaldehyde as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 10.08 (d, J=1.8 Hz, 1H), 8.06-8.12 (m, 1H), 7.79 (dd, J=8.0, 1.4 Hz, 1H), 7.69 (dd, J=10.6, 1.4 Hz, 1H), 4.52 (d, J=2.3 Hz, 2H).

Workup

  1. customThe solution was partitioned between EtOAc (50 mL) and brine (8 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customChromatographic purification of the residue (ISCO, 4 g, 0-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-df38c8c918fd40af935173b7b99f71b9
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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