3,4-Dimethoxybenzeneacetonitrile → HCID 69274237, compound

HRID 2222373Notes

Reaction equation

HRID 2222373 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=O.[CH3:11][O:12][CH2:13][CH2:14][O:15][CH2:16]Cl.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[CH2:23][C:24]#[N:25]>>[CH3:18][O:19][C:20]1[CH:21]=[C:22](/[C:23](=[CH:5]/[C:4]2[CH:7]=[CH:8][C:9]([O:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH3:16])=[C:2]([F:1])[CH:3]=2)/[C:24]#[N:25])[CH:26]=[CH:27][C:28]=1[O:29][CH3:30]

Participants

4

Reactant 3

HCID 667273,4-DimethoxybenzeneacetonitrileHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 5872503-Fluoro-4-hydroxybenzaldehyde

Product 1

HCID 69274237HCID 69274237, compoundYield 78%

Procedure

The hydroxyl group of 3-fluoro-4-hydroxybenzaldehyde (3.92 g) was protected by use of 2-methoxyethoxymethyl chloride (3.49 g) in accordance with (production process 1), to thereby produce an MEM form (4.98 g, yield: 78%). The resultant MEM form (4.98 g) and 3,4-dimethoxybenzyl cyanide (3.87 g) were subjected to condensation in accordance with process A of (production process 2), to thereby produce the target product (6.55 g, yield: 78%).

Workup

  1. customto thereby produce an MEM form (4.98 g, yield: 78%)

Sources & evidence

ORD record
ord-38b81cab877b40e48c8c2084e654faa5
Source dataset
uspto-grants-2008_05
Patent number
US07371773B2

Reaction notes

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