Boron tribromide → 8-(3,4-Dichlorobenzyl)-7-(pyrrolidin-1-yl)-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 510523Notes

Reaction equation

HRID 510523 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH2:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16]C)[CH:14]=2)[CH2:9][CH2:8][CH:7]1[N:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1.B(Br)(Br)Br>C(Cl)Cl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH2:5][CH:6]1[C:15]2[CH:14]=[C:13]([OH:16])[CH:12]=[CH:11][C:10]=2[CH2:9][CH2:8][CH:7]1[N:18]1[CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 574712301-(1-(3,4-Dichlorobenzyl)-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)pyrrolidine

Product 1

HCID 574712318-(3,4-Dichlorobenzyl)-7-(pyrrolidin-1-yl)-5,6,7,8-tetrahydronaphthalen-2-olYield 78%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(1-(3,4-Dichlorobenzyl)-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)pyrrolidine (1.6 g, 4.10 mmol) was dissolved in CH2Cl2 (100 ml) and BBr3 (1 molar in CH2Cl2, 12.3 ml, 12.3 mmol) was added at −10° C. It was stirred for 2 h after which time the temperature rose to room temperature. Ice water was added, the organic phase separated and the aqueous phase extracted with CH2Cl2. The combined organic layers were washed with saturated NaHCO3 and NaCl solution, dried over Na2SO4, and concentrated to afford a residue. The beige solid product (1.2 g, 78%) was obtained from precipitation in ethyl acetate.

Workup

  1. customrose to room temperature
  2. customthe organic phase separated
  3. extractionthe aqueous phase extracted with CH2Cl2
  4. washThe combined organic layers were washed with saturated NaHCO3 and NaCl solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto afford a residue

Sources & evidence

ORD record
ord-227ccfd871aa4afbbba5c8997253f34e
Source dataset
uspto-grants-2015_08
Patent number
US09096619B2

Reaction notes

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