Acetyl chloride → HCID 76568078, compound

HRID 1728128Notes

Reaction equation

[F:1][C:2]1[CH:9]=[CH:8][C:7]([I:10])=[CH:6][C:3]=1[CH:4]=O.[C:11]([Si:15]([CH3:30])([CH3:29])[O:16][CH2:17][CH2:18]OC1C=CC(I)=CC=1C=O)(C)(C)C.C[Si]([NH:35][Si](C)(C)C)(C)C.C([Li])CCC.C[Si](Cl)(C)C.C(N(CC)CC)C.C(Cl)(=O)C>>[F:1][C:2]1[CH:9]=[CH:8][C:7]([I:10])=[CH:6][C:3]=1[CH:4]=[N:35][C:17]([O:16][Si:15]([CH3:30])([CH3:29])[CH3:11])=[CH2:18]

Participants

Reactant 7

HCID 6367Acetyl chloride

HCID 6397Chlorotrimethylsilane

HCID 8471Triethylamine

HCID 13838Hexamethyldisilazane

HCID 162170582-Fluoro-5-iodobenzaldehyde

HCID 57565907HCID 57565907, compound

HCID 178418339Butyllithium

Product 1

HCID 76568078HCID 76568078, compound

Procedure

In a manner similar to the method described in example 190b, 2-fluoro-5-iodobenzaldehyde (2.62 g, 10.5 mmol) (Aldrich) was used as the starting material in place of 2-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-iodo-benzaldehyde to react with 1,1,3,3,3-hexamethyldisilazane (2.14 mL, 10.5 mmol), n-butyllithium (2.5 M, 4.2 mL, 10.5 mmol), trimethylsilyl chloride (1.33 mL, 10.5 mmol), triethylamine (1.9 mL, 13.6 mmol) and acetyl chloride (0.97 mL, 13.6 mmol) to give crude 1-(2-fluoro-5-iodophenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene as a yellow gum and used for the next step without further purification.

Sources & evidence

ORD record: ord-5269cd9532314a57833d45a8207f69b4
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07495007B2

Reaction notes

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