4-Bromobiphenyl → HCID 53652234, compound

HRID 1076086Notes

Reaction equation

HRID 1076086 reaction equation
BrC1C=CC(C2C=CC=CC=2[C:14]2([Cl:42])[CH:19]=[CH:18][C:17]([C:20]([C:22]3C=CC(Cl)(C4C=CC=CC=4C4C=CC(Br)=CC=4)C[CH:23]=3)=[O:21])=[CH:16][CH2:15]2)=CC=1.ClC1C=CC(C(Cl)=O)=CC=1.[Br:53][C:54]1[CH:59]=[CH:58][C:57]([C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)=[CH:56][CH:55]=1.[Cl-].[Al+3].[Cl-].[Cl-].[NH2-:70].[Na+]>C1C=CC=CC=1.C(#N)C>[OH:21][C:20]([C:63]1[CH:64]=[CH:65][C:60]([C:57]2[CH:56]=[CH:55][C:54]([Br:53])=[CH:59][CH:58]=2)=[CH:61][CH:62]=1)([C:17]1[CH:18]=[CH:19][C:14]([Cl:42])=[CH:15][CH:16]=1)[CH2:22][C:23]#[N:70]

Participants

8

Reactant 5

HCID 71014-BromobiphenylHCID 85014-Chlorobenzoyl chlorideHCID 24533Sodium amideHCID 6451240Aluminum(III) ChlorideHCID 86733398HCID 86733398, compound

Product 1

HCID 53652234HCID 53652234, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6342AcetonitrileSolvent

Procedure

4'-Bromo-4-biphenylyl-4-chlorophenyl ketone (74 g.), prepared by the reaction of p-chlorobenzoyl chloride and 4-bromobiphenyl in the presence of aluminium chloride, acetonitrile (12 g.) and sodamide (10 g.) were reacted in benzene by the method of Example 1 to give 3-hydroxy-3-(4'-bromo-4-biphenylyl)-3-p-chlorophenylpropionitrile, mp 160°-161°C after recrystallisation from benzene; λ max (ethanol) = 262 nm.

Sources & evidence

ORD record
ord-af431503afce4883aba669b04a769df8
Source dataset
uspto-grants-1976_05
Patent number
US03954869

Reaction notes

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