1-Bromo-3-fluorobenzene → HCID 22015761, compound

HRID 916227Notes

Reaction equation

HRID 916227 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[CH:3]=1.[F:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[CH:13]=[O:14]>C1COCC1>[F:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[CH:13]([OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[CH:3]=1

Participants

4

Reactant 2

HCID 140821-Bromo-3-fluorobenzeneHCID 676963-Fluoro-p-anisaldehyde

Product 1

HCID 22015761HCID 22015761, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of Mg° turnings (2.45 g, 101 mmol), 1-bromo-3-fluorobenzene (17.69 g, 100 mmol), and dry THF (200 mL) was carefully heated to reflux for 30 min. While still refluxing, 3-fluoro-p-anisaldehyde (15.3g, 99.3 mmol) in THF (100 mL) was added over a period of 5 min. The reaction temperature was maintained for 30 min. cooled to room temperature, and then the reaction was quenched with satd. aq. NH4Cl (200 mL). The organic layer was separated, washed with satd. aq. NaCl (2×200 mL), dried (anh. Na2SO4) and rotary evaporated to yield 23.5 g (94.4%) of product as an orange-brown oil.

Workup

  1. temperaturewas carefully heated
  2. temperatureto reflux for 30 min
  3. temperatureWhile still refluxing
  4. temperatureThe reaction temperature was maintained for 30 min.
  5. customthe reaction was quenched with satd
  6. customThe organic layer was separated
  7. washwashed with satd
  8. dry with materialaq. NaCl (2×200 mL), dried (anh. Na2SO4)
  9. customrotary evaporated

Sources & evidence

ORD record
ord-24a00800405840bfa85255a69dabca36
Source dataset
uspto-grants-2007_09
Patent number
US07268166B2

Reaction notes

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