Boron tribromide → HCID 21850086, compound

HRID 617912Notes

Reaction equation

HRID 617912 reaction equation
Cl.C[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:20]C)[CH:16]=3)[C:11]=2[C:22]2[CH:23]=[C:24]([O:28][CH2:29][CH2:30][N:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)[CH:25]=[CH:26][CH:27]=2)=[CH:6][CH:5]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([OH:20])[CH:16]=3)[C:11]=2[C:22]2[CH:23]=[C:24]([O:28][CH2:29][CH2:30][N:31]3[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]3)[CH:25]=[CH:26][CH:27]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 25134Boron tribromide2×HCID 9935882HCID 9935882, compound

Product 1

HCID 21850086HCID 21850086, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1.5 g (3 mmol) of 1-[2-[3-[2-(4-methoxyphenyl)-6-methoxynaphth-1-yl]phenyloxy]ethyl]piperidine hydrochloride was dissolved in 100 mL of CH2Cl2 and cooled to 0° C. 0.7 mL (7.5 mmol) of BBr3 was slowly added and the reaction allowed to proceed for twenty-four hours. An additional 3 mL of BBr3 was added and the reaction was continued for two more hours. The reaction was quenched by pouring into water, followed by three extractions with EtOH--CHCl3 (1:9) (v/v). The organic extracts were combined, washed twice with brine, dried with Na2SO4, and evaporated to dryness. The final product was purified by chromatography on a silica gel column eluted with a linear gradient begining with CH2Cl2 and ending with CH2Cl2 --MeOH (9:1) (v/v). This yielded 0.5 g of the title compound as a white amorphous powder.

Workup

  1. waitto proceed for twenty-four hours
  2. customThe reaction was quenched
  3. additionby pouring into water
  4. extractionfollowed by three extractions with EtOH--CHCl3 (1:9) (v/v)
  5. washwashed twice with brine
  6. dry with materialdried with Na2SO4
  7. customevaporated to dryness
  8. customThe final product was purified by chromatography on a silica gel column
  9. washeluted with a linear gradient

Sources & evidence

ORD record
ord-ec33704d613241a1b45dfc66ed58d272
Source dataset
uspto-grants-1999_09
Patent number
US05952350

Reaction notes

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