2-Fluoro-4,5-dimethoxybenzaldehyde → 2-Fluoro-4-hydroxy-5-methoxybenzaldehyde

HRID 1908083Notes

Reaction equation

HRID 1908083 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[F:5][C:6]1[CH:13]=[C:12]([O:14]C)[C:11]([O:16][CH3:17])=[CH:10][C:7]=1[CH:8]=[O:9]>C(Cl)Cl>[F:5][C:6]1[CH:13]=[C:12]([OH:14])[C:11]([O:16][CH3:17])=[CH:10][C:7]=1[CH:8]=[O:9]

Participants

4

Reactant 2

HCID 6035952-Fluoro-4,5-dimethoxybenzaldehydeHCID 6451240Aluminum(III) Chloride

Product 1

HCID 5981552-Fluoro-4-hydroxy-5-methoxybenzaldehydeYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

AlCl3 (8.69 g, 65.2 mmol) was added to a solution of 2-fluoro-4,5-dimethoxy-benzaldehyde (2.00 g, 10.9 mmol) in DCM (100 mL) under an atmosphere of argon. The reaction mixture was allowed to stir at room temperature for 16 h. The reaction mixture was slowly quenched with water. The layers were separated and the aqueous layer was then extracted with ethyl acetate (3×). The combined organic layers were dried over sodium sulfate and then evaporated to dryness to yield 2-fluoro-4-hydroxy-5-methoxy-benzaldehyde (1.82 g, 98%) as an off white solid. ESI-MS m/z calc. 170.0. found 171.0 (M+1)+. Retention time: 0.84 minutes (3 min run). 1H NMR (400 MHz, DMSO) δ 10.04 (s, 1H), 7.22 (d, J=6.7 Hz, 1H), 6.73 (d, J=11.9 Hz, 1H), 3.81 (s, 3H).

Workup

  1. customThe reaction mixture was slowly quenched with water
  2. customThe layers were separated
  3. extractionthe aqueous layer was then extracted with ethyl acetate (3×)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-38b2b6e06f6c45739481ba8b9c743d73
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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