Benzyl Bromide → 4-(Benzyloxy)-3-nitrobenzaldehyde

HRID 990111

반응식

HRID 990111 반응식
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:13]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 181694-Hydroxy-3-nitrobenzaldehyde

생성물 1

HCID 70235544-(Benzyloxy)-3-nitrobenzaldehyde

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Substituted benzyl bromide compounds can also be prepared from commercially available substituted benzaldehydes, benzoic acids and benzoic esters by first converting these compounds to the corresponding alcohol. Exemplary synthetic methodology to provide substituted benzyl bromide from benzyl aldehyde is described below. For example, as illustrated in Scheme 12, treatment of 4-hydroxy-3-nitro-benzaldehyde 73 with benzyl bromide in the presence of K2CO3 in DMF at 65° C. gives 4-benzyloxy-3-nitro-benzaldehyde 74. Reduction of compound 74 in methanol with NaBH4 affords the alcohol 75 and subsequent bromination using PBr3 in diethyl ether provides the desired bromide compound 76.

출처 및 근거

ORD 기록
ord-0eaa3129489645d48cc52af19fec94cd
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06458829B1

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