4-Bromoanisole → HCID 23326077, compound

HRID 1980125Notes

Reaction equation

HRID 1980125 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[Mg].O1CCCC1.[F:16][C:17]1[CH:35]=[CH:34][C:20]([C:21]([CH:23]2[CH2:28][CH2:27][N:26]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:25][CH2:24]2)=[O:22])=[CH:19][CH:18]=1>CC1C=CC=CC=1.C(O)(=O)C>[F:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]([OH:22])([C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=2)[CH:23]2[CH2:24][CH2:25][N:26]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:27][CH2:28]2)=[CH:34][CH:35]=1

Participants

7

Reactant 4

HCID 77304-BromoanisoleHCID 8028Tetrahydrofuran2×HCID 5462224MagnesiumHCID 23326081HCID 23326081, compound

Product 1

HCID 23326077HCID 23326077, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Conditions

Temperature
10 °C

Procedure

To a stirred and refluxing Grignard complex previously prepared starting from 112.2 parts of 1-bromo-4-methoxybenzene, 15 parts of magnesium and 540 parts of tetrahydrofuran was added dropwise a solution of 84 parts of ethyl 4-(4-fluorobenzoyl)-1-piperidinecarboxylate in 360 parts of tetrahydrofuran. Upon completion, stirring was continued for 2 hours at reflux. After cooling to 10° C., the reaction mixture was poured onto a mixture of 300 parts of crushed ice and 40 parts of acetic acid. The whole was stirred for 5 minutes. 360 Parts of methylbenzene were added. The organic layer was separated, dried, filtered and evaporated, yielding 100 parts of ethyl 4-[(4-fluorophenyl)hydroxy-(4-methoxyphenyl)-methyl]-1-piperidinecarboxylate as an oily residue (intermediate 10).

Workup

  1. temperaturerefluxing Grignard complex
  2. custompreviously prepared
  3. stirringUpon completion, stirring
  4. temperatureat reflux
  5. stirringThe whole was stirred for 5 minutes
  6. customThe organic layer was separated
  7. customdried
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-e1410033393e416fb3a297ea564ea4d6
Source dataset
uspto-grants-1984_11
Patent number
US04485107

Reaction notes

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