Hydrochloric Acid → HCID 20184923, compound

HRID 2309303Notes

Reaction equation

HRID 2309303 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:4]([F:14])[CH:3]=1.[Mg].II.BrC1C=CC(C2C=CC=CC=2)=CC=1F.[CH2:32]([CH:35]1[CH2:40][CH2:39][C:38](=[O:41])[CH2:37][CH2:36]1)[CH2:33][CH3:34].Cl>C(OCC)C>[F:14][C:4]1[CH:3]=[C:2]([C:38]2([OH:41])[CH2:39][CH2:40][CH:35]([CH2:32][CH2:33][CH3:34])[CH2:36][CH2:37]2)[CH:7]=[CH:6][C:5]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 807IodineHCID 1424824-PropylcyclohexanoneHCID 5210634-Bromo-2-fluoro-1,1'-biphenylHCID 5462224MagnesiumHCID 11715782HCID 11715782, compound

Product 1

HCID 20184923HCID 20184923, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A few ml of a solution of 4-bromo-2-fluorobiphenyl (50 gram) in diethyl ether (150 ml) was added to magnesium turnings (5.3 gram) and diethyl ether (25 ml) under nitrogen. A crystal of iodine was added and reaction was initiated by warming. The remainder of the solution of 4-bromo-3-fluorobiphenyl was then added at a rate fast enough to sustain vigorous refluxing. After boiling for 1 hour, the solution of the Grignard reagent was cooled to 20° C. and then a solution of 4-n-propylcyclohexanone (27.9 gram) in diethyl ether (75 ml) was added over 30 minutes. After stirring for 1 hour, the mixture was poured onto 15% hydrochloric acid (2 liter) and the product extracted with ether (2×300 ml). The combined extracts were washed with water, dried and evaporated. The residue was crystallised from petroleum ether (b.p. 60°-80°, 120 ml) to give 1-(2-fluoro-4-biphenylyl)-4-propyl cyclohexane-1-ol as pale yellow crystals, m.p. 45°-72° (37.2 gram: 61.2% theory) (isomer ratio by glc 60.6: 39.4).

Workup

  1. customreaction
  2. temperatureby warming
  3. extractionthe product extracted with ether (2×300 ml)
  4. washThe combined extracts were washed with water
  5. customdried
  6. customevaporated
  7. customThe residue was crystallised from petroleum ether (b.p. 60°-80°, 120 ml)

Sources & evidence

ORD record
ord-bea9b5847bc545a2a681a837d33e6446
Source dataset
uspto-grants-1987_09
Patent number
US04695131

Reaction notes

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