Boron tribromide → 7-Amino-8-benzyl-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 82862Notes

Reaction equation

HRID 82862 reaction equation
[CH2:1]([CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18]C)[CH:16]=2)[CH2:11][CH2:10][CH:9]1[NH2:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>ClCCl>[NH2:20][CH:9]1[CH:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:17]2[CH:16]=[C:15]([OH:18])[CH:14]=[CH:13][C:12]=2[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 866856811-Benzyl-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine

Product 1

HCID 866856807-Amino-8-benzyl-5,6,7,8-tetrahydronaphthalen-2-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-benzyl-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine (2.56 g, 9.57 mmol) in dry dichloromethane (47.4 mL) under Argon at 0° C. 1M BBr3 in dichloromethane (23.93 mL, 23.93 mmol) was added. The cooling bath was removed and the reaction was allowed to reach room temperature overnight. The reaction was quenched with water, and 1 M NaOH was added to alkalinity. The organic layer was separated and the aqueous phase was extracted with dichloromethane (4×50 mL). The collected organic extracts were concentrated until the product precipitated as a green solid. The solid was collected via filtration and washed with cold dichloromethane (ca. 10 mL). The solid obtained was dried to a gray-greenish powder (2.233 g, 8.81 mmol, 92%).

Workup

  1. customat 0° C
  2. customThe cooling bath was removed
  3. customThe reaction was quenched with water, and 1 M NaOH
  4. additionwas added to alkalinity
  5. customThe organic layer was separated
  6. extractionthe aqueous phase was extracted with dichloromethane (4×50 mL)
  7. concentrationThe collected organic extracts were concentrated until the product
  8. customprecipitated as a green solid
  9. filtrationThe solid was collected via filtration
  10. washwashed with cold dichloromethane (ca. 10 mL)
  11. customThe solid obtained

Sources & evidence

ORD record
ord-83205c0e46b84ae9949edeeaf0fff9f4
Source dataset
uspto-grants-2014_09
Patent number
US08846741B2

Reaction notes

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