2-Fluorobenzoyl chloride → Benzophenone

HRID 1154584Notes

Reaction equation

O1C2C=C3OC=CC3=CC=2CN1.COC(/C=C/C1[CH:24]=[C:23](O)[C:22]2[O:26][CH:27]([C:33]3[CH:34]=[CH:35][C:36](O)=[C:37](O)[CH:38]=3)[CH:28]([C:29](OC)=O)[C:21]=2C=1)=O.FC1C=CC=CC=1C(Cl)=O>>[C:27]([C:28]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:29]=1)(=[O:26])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

Reactant 3

HCID 98082-Fluorobenzoyl chloride

HCID 5857314Dihydrobezofuran

HCID 20434050Dihydrofuro[3,2-f]-1,2-benzisoxazole

Product 1

HCID 3102Benzophenone

Procedure

Reaction Scheme 2 proved to be useful for preparing compounds with different substituents at the 8-position of the dihydrofuro[3,2-f]-1,2-benzisoxazole nucleus. In this process, a dihydrobenzofuran intermediate (5) (prepared in Scheme 3) was subjected to a Friedel-Crafts reaction with o-fluorobenzoyl chloride to give the benzophenone intermediates (6) or (7). Use of mild reaction conditions in this acylation reaction gave the methyl ether (6) whereas more vigorous conditions led directly to the demethylated product (7). Reaction of the benzophenone (7) with hydroxylamine hydrochloride gave the corresponding oxime (8) which was converted to the oxime acetate (9) with acetic anhydride. Cyclization to (10) was achieved by treatment of the oxime acetate intermediate (9) with sodium hydride in N,N-dimethylformamide solution. The final carboxylic acid derivatives (11) were obtained from (10) by a hydrolysis reaction using potassium hydroxide in aqueous ethanol.

Workup

customReaction Scheme 2

Sources & evidence

ORD record: ord-b532f96d535349ab9bffe2e4504f3b00
Source dataset: uspto-grants-1984_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04490384

Reaction notes

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