4-Bromobiphenyl → 5-(1,1'-Biphenyl-4-yl)-4-pentyn-1-ol

HRID 2106877Notes

Reaction equation

HRID 2106877 reaction equation
C(O)CCC#C.BrC1C=CC(C2C=CC=CC=2)=CC=1.[C:20]1([C:26]2[CH:31]=[CH:30][C:29]([C:32]#[C:33][CH2:34][CH2:35][CH:36]=[O:37])=[CH:28][CH:27]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(NC(=O)/C=C/CCC#CC1C=CC(C2C=CC=CC=2)=CC=1)C(C)C>>[C:20]1([C:26]2[CH:31]=[CH:30][C:29]([C:32]#[C:33][CH2:34][CH2:35][CH2:36][OH:37])=[CH:28][CH:27]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 4

HCID 71014-BromobiphenylHCID 793464-Pentyn-1-olHCID 23049314HCID 23049314, compoundHCID 230493365-(4'-Phenylphenyl)-4-pentyn-1-al

Product 1

HCID 230493185-(1,1'-Biphenyl-4-yl)-4-pentyn-1-ol

Procedure

5-(4'-phenylphenyl)-4-pentyn-1-ol was prepared from 4-pentyn-1-ol and 4'-bromobiphenyl as in Example 15, and converted into 5-(4'-phenylphenyl)-4-pentyn-1-al by the method of Example 9. N-isobutyl 7-(4'-phenylphenyl)-(2E)-hepten-6-ynamide was then prepared from 5-(4'-phenylphenyl)-4-pentyn-1-pentyn-1-al and N-isobutylacetamidotriphenylphosphonium chloride as in Example 9 and semi-hydrogenated as in Example 9 to give N-isobutyl 7-(4'-phenylphenyl)-(2E,6Z)-heptadienamide.

Sources & evidence

ORD record
ord-6bf2a4f99be7499cb45354564cf59d56
Source dataset
uspto-grants-1990_06
Patent number
US04931469

Reaction notes

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