Benzyl Bromide → HCID 23326074, compound

HRID 1980140Notes

Reaction equation

HRID 1980140 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[OH:9])=[CH:4][CH:3]=1.[Br:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(#N)C>[Br-:23].[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)([OH:9])[C:10]2[CH:11]=[CH:12][N+:13]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:14][CH:15]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 2960505HCID 2960505, compound

Product 1

HCID 23326074HCID 23326074, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred mixture of 89.2 parts of α,α-bis(4-fluorophenyl)-4-pyridinemethanol and 720 parts of acetonitrile were added dropwise 56.5 parts of (bromomethyl)benzene at reflux temperature. Upon completion, stirring was continued for 22 hours at reflux. The reaction mixture was allowed to stand over week-end at room temperature. The product was filtered off and set aside. The filtrate was concentrated to a volume of 50 parts. The product was allowed to crystallize. It was filtered off and washed, together with the product which was set aside (see above), with 2,2'-oxybispropane and dried, yielding 139.5 parts (99.2%) of 4-[bis(4-fluorophenyl)hydroxymethyl]-1-(phenylmethyl)pyridinium bromide (intermediate 27).

Workup

  1. temperatureat reflux temperature
  2. temperatureat reflux
  3. waitto stand over week-end at room temperature
  4. filtrationThe product was filtered off
  5. concentrationThe filtrate was concentrated to a volume of 50 parts
  6. customto crystallize
  7. filtrationIt was filtered off
  8. washwashed, together with the product which
  9. dry with materialwith 2,2'-oxybispropane and dried

Sources & evidence

ORD record
ord-f256792197334240b80f14b647da595c
Source dataset
uspto-grants-1984_11
Patent number
US04485107

Reaction notes

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