Methanol → HCID 19782189, compound

HRID 1612973Notes

Reaction equation

HRID 1612973 reaction equation
C[O:2][C:3]1[C:4]2[C:9]([C:10]3[CH:11]=[CH:12][CH2:13][C:14](=O)[C:15]=3[CH:16]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.B(Br)(Br)Br.C[OH:23]>C(Cl)Cl>[OH:2][C:3]1[CH:16]=[C:15]2[C:10]([CH2:11][CH2:12][CH2:13][CH2:14]2)=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=[O:23]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 67835205HCID 67835205, compound

Product 1

HCID 19782189HCID 19782189, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

47.4 g (0.22 mol) of the 9-methoxy-phenanthrenone from Example 3 are dissolved in 605 ml of absolute methylene chloride and 440 ml of a 1 molar solution of boron tribromide in methylene chloride are added dropwise at -78° C. The mixture is stirred at -78° C. for 0.5 h, then at +20° C. for 3 h, cooled again to -78° C. and 620 ml of methanol is slowly added. The mixture is allowed to come to 20° C. and is evaporated. The residue is partitioned between 200 ml of CH2Cl2 and 200 ml of 1N NaOH solution, and the NaOH phase is separated and acidified to pH 1 using concentrated HCl solution with ice cooling. The precipitate is filtered off and dried in a high vacuum.

Workup

  1. waitat +20° C. for 3 h
  2. temperaturecooled again to -78° C.
  3. customto come to 20° C.
  4. customis evaporated
  5. customThe residue is partitioned between 200 ml of CH2Cl2 and 200 ml of 1N NaOH solution
  6. customthe NaOH phase is separated
  7. filtrationThe precipitate is filtered off
  8. customdried in a high vacuum

Sources & evidence

ORD record
ord-ba37c2d1ef3241cb863baf212cbc454d
Source dataset
uspto-grants-1993_03
Patent number
US05191092

Reaction notes

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