Aluminum(III) Chloride → Methyl 2-fluoro-4-formyl-6-hydroxybenzoate

HRID 924657Notes

Reaction equation

HRID 924657 reaction equation
C(C1C=CC(C(OC)=O)=C(O)C=1)=O.[F:14][C:15]1[CH:24]=[C:23]([CH:25]=[O:26])[CH:22]=[C:21]([O:27]C)[C:16]=1[C:17]([O:19][CH3:20])=[O:18].[Al+3].[Cl-].[Cl-].[Cl-]>>[F:14][C:15]1[CH:24]=[C:23]([CH:25]=[O:26])[CH:22]=[C:21]([OH:27])[C:16]=1[C:17]([O:19][CH3:20])=[O:18]

Participants

4

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 21626741Methyl 4-formyl-2-hydroxybenzoateHCID 86681499Methyl 2-fluoro-4-formyl-6-methoxybenzoate

Product 1

HCID 86669343Methyl 2-fluoro-4-formyl-6-hydroxybenzoateYield 97.1%

Procedure

Followed procedure described in Intermediate 5, step 3 starting with methyl 2-fluoro-4-formyl-6-methoxybenzoate (280 mg, 1.3 mmol) and AlCl3 (350 mg, 2.6 mmol) where reaction was complete after refluxing 10 min. Isolated 250 mg of Intermediate 7, yield 96%.

Workup

  1. temperatureafter refluxing 10 min

Sources & evidence

ORD record
ord-9ff96bb5148345a9b04896f7a1f23f18
Source dataset
uspto-grants-2016_03
Patent number
US09283213B2

Reaction notes

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