Triethylamine → 4-[(4-Ethoxy-2,3-difluorophenyl)ethynyl]-4'-propyl-1,1'-biphenyl

HRID 1198335Notes

Reaction equation

HRID 1198335 reaction equation
BrBr.[CH2:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24]C(CCC)=CC=3)=CC=2)=C)=[C:8]([F:29])[C:7]=1[F:30])[CH3:4].C(N([CH2:36][CH3:37])CC)C.C([N-][CH:42]([CH3:44])[CH3:43])(C)C.[Li+]>ClCCl.C(#N)C.C1COCC1>[CH2:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:14][C:19]2[CH:18]=[CH:17][C:20]([C:37]3[CH:36]=[CH:8][C:7]([CH2:44][CH2:42][CH3:43])=[CH:6][CH:11]=3)=[CH:25][CH:24]=2)=[C:8]([F:29])[C:7]=1[F:30])[CH3:4]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 24408BromineHCID 2724682Lithium diisopropylamideHCID 19103502HCID 19103502, compound

Product 1

HCID 678645704-[(4-Ethoxy-2,3-difluorophenyl)ethynyl]-4'-propyl-1,1'-biphenyl

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

0.065 mol of bromine are added to a stirred solution of 0.065 mol of this ethen derivative in a mixture of 100 ml of dichloromethane and 50 ml of acetonitrile. After addition of 10 g of triethylamine and customary working up the crude product is dissolved in 50 ml of THF. 0.13 mol of lithium diisopropylamide in 120 ml of THF are added dropwise to this solution at -50° C. Customary working up gives 1-(4-Ethoxy-2,3-difluorophenyl)-2-(4'-propylbiphenyl-4-yl)-ethine.

Sources & evidence

ORD record
ord-60e7d7fecfa248db9756eefc78bf9e50
Source dataset
uspto-grants-1994_01
Patent number
US05279764

Reaction notes

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