Hydrogen Bromide → N-((R)-6-bromo-1,2,3,4-tetrahydronaphthalen-2-yl)-4-methoxybenzamide

HRID 77415Notes

Reaction equation

HRID 77415 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C@@H:7]([NH:12][C:13](=[O:22])[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[CH2:6][CH2:5]2.Br>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C@@H:7]([NH:12][C:13](=[O:22])[C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1)[CH2:6][CH2:5]2.[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C@H:7]([NH:12][C:13](=[O:22])[C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1)[CH2:6][CH2:5]2

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 66663809N-((S)-6-bromo-1,2,3,4-tetrahydronaphthalen-2-yl)-4-methoxybenzamide

Product 2

HCID 10247920N-((R)-6-bromo-1,2,3,4-tetrahydronaphthalen-2-yl)-4-methoxybenzamideHCID 66663809N-((S)-6-bromo-1,2,3,4-tetrahydronaphthalen-2-yl)-4-methoxybenzamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of N—((S)-6-bromo-1,2,3,4-tetrahydronaphthalen-2-yl)-4-methoxybenzamide (3.0 g), glacial acetic acid (2 ml) and HBr (20 ml; 48% in water) was heated in a closed glass vessel in a microwave reactor to 150° C. for 25 minutes. The precipitate obtained after cooling was filtered off. The product was thus obtained with the molecular weight of 346.23 (C17H16BrNO2); MS (ESI): 346 (M+H+). Both N—((S)-6-bromo-1,2,3,4-tetrahydronaphthalen-2-yl)-4-methoxybenzamide and N—((R)-6-bromo-1,2,3,4-tetrahydronaphthalen-2-yl)-4-methoxybenzamide can be obtained by literature methods (J. Org. Chem. 1995, 60, 4324).

Workup

  1. customThe precipitate obtained
  2. temperatureafter cooling
  3. filtrationwas filtered off
  4. customThe product was thus obtained with the molecular weight of 346.23 (C17H16BrNO2)

Sources & evidence

ORD record
ord-bf77b31043e1413d9891f860a631d1a6
Source dataset
uspto-grants-2014_09
Patent number
US08841290B2

Reaction notes

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