Boron tribromide → Ethyl 2-(6-hydroxy-1,2,3,4-tetrahydronaphthalen-1-yl)acetate

HRID 445809Notes

Reaction equation

HRID 445809 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:8][CH2:7][CH2:6]2.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:8][CH2:7][CH2:6]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 13420659Ethyl 2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)acetate

Product 1

HCID 57835772Ethyl 2-(6-hydroxy-1,2,3,4-tetrahydronaphthalen-1-yl)acetateYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)acetate (513) (0.708 g, 2.85 mmol) in dichloromethane (28 mL) at 0° C. was added boron tribromide (0.809 mL, 8.56 mmol). The solution was stirred for 2 hours and quenched with ethanol (5 mL) followed by a saturated solution of sodium bicarbonate (5 mL). The organic layer was separated, dried over sodium sulfate, filtered and concentrated in vacuo to obtain the intermediate ethyl 2-(6-hydroxy-1,2,3,4-tetrahydronaphthalen-1-yl)acetate (514) (0.600 g, 90.0%) as an oil residue.

Workup

  1. customquenched with ethanol (5 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-591cc5995bec44f48cf998aa34cdf532
Source dataset
uspto-grants-2013_07
Patent number
US08476308B2

Reaction notes

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