5-Bromo-2-fluorobenzaldehyde → HCID 54595143, compound

HRID 1365064Notes

Reaction equation

HRID 1365064 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]([CH:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[OH:5])[CH:6]=1

Participants

4

Reactant 2

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

Product 1

HCID 54595143HCID 54595143, 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. Purification using silica gel chromatography provided (5-bromo-2-fluorophenyl)(phenyl)methanol as a colorless oil. H1 NMR (d6-dmso): 7.68 (dd, 1H), 7.46 (m, 1H), 7.32 (m, 4H), 7.23 (m, 1H), 7.12 (dd, 1H), 6.16 (d, 1H), 5.89 (d, 1H).

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. customPurification

Sources & evidence

ORD record
ord-fd2862c3133949af854a8c3bbcfe44ae
Source dataset
uspto-grants-2011_02
Patent number
US07888503B2

Reaction notes

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