HCID 118006008, compound → HCID 118005892, compound

HRID 1049626Notes

Reaction equation

HRID 1049626 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[Br:12][C:13]1[CH:22]=[C:21]([F:23])[CH:20]=[C:19]2[C:14]=1[CH:15]=[CH:16][C:17]([CH2:24][OH:25])=[CH:18]2>C(Cl)Cl>[Br:12][C:13]1[CH:22]=[C:21]([F:23])[CH:20]=[C:19]2[C:14]=1[CH:15]=[CH:16][C:17]([CH:24]=[O:25])=[CH:18]2

Participants

4

Reactant 2

HCID 118006008HCID 118006008, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 118005892HCID 118005892, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridinium chlorochromate (PCC, 1.9 g, 9.0 mmol) was added to a solution of 31 (1.1 g, 4.5 mmol) in DCM (15 mL), and the mixture was stirred for 2 h prior to filtration through a short pad of silica gel. The filtrate was then concentrated rotary evaporation, and purified by column chromatography to give 5-bromo-7-fluoro-2-naphthaldehyde (32) (88%). 1H NMR (400 MHz, CDCl3) δ 10.20 (s, 1H), 8.34 (d, J=8.8 Hz, 1H), 8.29 (s, 1H), 8.01 (d, J=8.8 Hz, 1H), 7.77 (dd, J=8.0, 2.3 Hz, 1H), 7.64 (d, J=8.6 Hz, 1H). GC-MS (ES) for C11H6BrFO [M+1]+253.

Workup

  1. filtrationto filtration through a short pad of silica gel
  2. concentrationThe filtrate was then concentrated rotary
  3. customevaporation
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-2a5f896ee4524b499bd4f7c4708b50da
Source dataset
uspto-grants-2016_07
Patent number
US09382245B2

Reaction notes

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