4-Fluorobiphenyl → 1-Chloro-3-(4'-fluoro-4-biphenylyl)-butan-3-ol

HRID 2420603Notes

Reaction equation

HRID 2420603 reaction equation
[Cl:1][CH2:2][CH2:3][CH:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)[CH3:5].FC1C=CC(C2C=CC=CC=2)=CC=1.ClCCC(Cl)=[O:36].FC1C=CC(C2C=CC(C(=O)CCCl)=CC=2)=CC=1.C[Mg]I>>[Cl:1][CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)=[CH:8][CH:7]=1)([OH:36])[CH3:5]

Participants

6

Reactant 5

HCID 94614-FluorobiphenylHCID 693643-Chloropropionyl chlorideHCID 203020144-(4-Chlorobutan-2-yl)-4'-fluoro-1,1'-biphenylHCID 203027244'-Fluoro-4-(3-chloropropionyl)-biphenylHCID 178418373HCID 178418373, compound

Product 1

HCID 203028961-Chloro-3-(4'-fluoro-4-biphenylyl)-butan-3-ol

Procedure

A solution of 26.25 g of 1-chloro-3-(4'-fluoro-4-biphenylyl)-butane [obtainable by a Friedel-Crafts reaction of 4-fluoro-biphenyl with 3-chloropropionyl chloride to give 4'-fluoro-4-(3-chloropropionyl)-biphenyl (m.p. 96° - 97° ), reaction with CH3MgI to give 1-chloro-3-(4'-fluoro-4-biphenylyl)-butan-3-ol (m.p. 78° - 79° ) and reduction using HI] in 150 ml of absolute ethanol is added dropwise at 0° to a solution of 10 g of NH3 in 150 ml of absolute ethanol. The solution is stirred for a further 2 hours at 20°, concentrated and worked up with aqueous sodium hydroxide solution and ether to give 3-(4'-fluoro-4-biphenylyl)-butylamine; hydrochloride, m.p. 222° - 224°.

Workup

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Sources & evidence

ORD record
ord-8cedfefdb8eb4b668a3a9f072f1e070c
Source dataset
uspto-grants-1978_08
Patent number
US04110447

Reaction notes

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