5-Bromo-2-fluorobenzaldehyde → HCID 43160375, compound

HRID 1365063Notes

Reaction equation

HRID 1365063 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][C:3]=1[CH:4]=[O:5].[C:11]1([Mg]Br)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>O1CCCC1>[Br:10][C:7]1[CH:8]=[CH:9][C:2]([F:1])=[C:3]([C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:5])[CH:6]=1

Participants

4

Reactant 2

HCID 7363275-Bromo-2-fluorobenzaldehydeHCID 178418255HCID 178418255, compound

Product 1

HCID 43160375HCID 43160375, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A round-bottomed flask was charged with 2-fluoro-5-bromobenzaldehyde (1.01 g) and tetrahydrofuran (50 mL), placed under a nitrogen atmosphere then cooled to −78° C. To this solution was added a 1M solution of phenylmagnesium bromide (5 mL). The reaction was stirred for 15 min then removed from the cold bath and allowed to warm to 0° C. Quenching was achieved by the addition of water and diethyl ether. The organic layer was collected, dried over magnesium sulfate then concentrated to an oil. The residue was dissolved in methylene chloride (100 mL) and treated with Dess-Martin periodinane (2.12 g) at room temperature. The reaction mixture was stirred for 30 min then loaded directly onto a silica gel pad. The pad was eluted with methylene chloride, and the desired fractions were combined and concentrated to dryness to provide (5-bromo-2-fluorophenyl)(phenyl)methanone as a yellow oil (0.80 g). 1H NMR (400 MHz, DMSO-D6) δ ppm 7.8 (m, 1 H) 7.7 (m, 3 H) 7.6 (m, 1 H) 7.5 (m, 2 H) 7.3 (m, 1 H)

Workup

  1. customthen removed from the cold bath
  2. temperatureto warm to 0° C
  3. customQuenching
  4. additionwas achieved by the addition of water and diethyl ether
  5. customThe organic layer was collected
  6. dry with materialdried over magnesium sulfate
  7. concentrationthen concentrated to an oil
  8. dissolutionThe residue was dissolved in methylene chloride (100 mL)
  9. additiontreated with Dess-Martin periodinane (2.12 g) at room temperature
  10. stirringThe reaction mixture was stirred for 30 min
  11. washThe pad was eluted with methylene chloride
  12. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-d855db6652a643a19da85f51e7452c88
Source dataset
uspto-grants-2011_02
Patent number
US07888503B2

Reaction notes

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