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2-(4-Bromomethyl-3-fluorophenyl)benzoxazole → 4-(5,7-Dichlorobenzoxazol-2-yl)phenylacetonitrile

HRID 2071475
Notes
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Reaction equation

HRID 2071475 reaction equation
[Cl:1][C:2]1[C:10]2[O:9][C:8]([C:11]3[CH:16]=[CH:15][C:14]([CH2:17]Br)=[CH:13][CH:12]=3)=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Cl:19][C:20]1[CH:21]=[C:22]([Cl:37])[C:23]2[O:27][C:26]([C:28]3[CH:33]=[CH:32][C:31]([CH2:34]Br)=[CH:30][CH:29]=3)=[N:25][C:24]=2[CH:36]=1.[O:38]1[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=2[N:40]=[C:39]1[C:47]1[CH:55]=[CH:54][CH:53]=[C:49]2[CH2:50][CH:51](Br)[C:48]=12.BrCC1C=CC([C:64]2OC3C=CC=CC=3[N:68]=2)=CC=1F>>[Cl:1][C:2]1[C:10]2[O:9][C:8]([C:11]3[CH:16]=[CH:15][C:14]([CH2:17][C:24]#[N:25])=[CH:13][CH:12]=3)=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Cl:19][C:20]1[CH:21]=[C:22]([Cl:37])[C:23]2[O:27][C:26]([C:28]3[CH:33]=[CH:32][C:31]([CH2:34][C:39]#[N:40])=[CH:30][CH:29]=3)=[N:25][C:24]=2[CH:36]=1.[O:38]1[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=2[N:40]=[C:39]1[C:47]1[CH:55]=[CH:54][CH:53]=[C:49]2[CH2:50][CH:51]([C:64]#[N:68])[C:48]=12
ParticipantsProcedureSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 214138052-(4-Bromomethyl-3-fluorophenyl)benzoxazoleHCID 214138205,7-Dichloro-2-(4-bromomethylphenyl)benzoxazoleHCID 214138597-Chloro-2-(4-bromomethylphenyl)benzoxazoleHCID 1317101184-(Benzoxazol-2-yl)-1-bromobenzocyclobutene

Product 3

HCID 214138514-(5,7-Dichlorobenzoxazol-2-yl)phenylacetonitrile
HCID 21413858
4-(7-Chlorobenzoxazol-2-yl)-phenylacetonitrile
HCID 1317101174-(Benzoxazol-2-yl)-1-cyanobenzocyclobutene

Procedure

When 7-chloro-2-(4-bromomethylphenyl)benzoxazole, 5,7-dichloro-2-(4-bromomethylphenyl)benzoxazole and 4-(benzoxazol-2-yl)-1-bromobenzocyclobutene are used in place of 2-(4-bromomethyl-3-fluorophenyl)benzoxazole in the above example, there is obtained 4-(7-chlorobenzoxazol-2-yl)-phenylacetonitrile, 4-(5,7-dichlorobenzoxazol-2-yl)phenylacetonitrile, and 4-(benzoxazol-2-yl)-1-cyanobenzocyclobutene, respectively.

Sources & evidence

ORD record
ord-54260708d3aa49b498640682edba388e
Source dataset
uspto-grants-1977_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04046905

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes