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

HRID 1913814Notes

Reaction equation

HRID 1913814 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 to 150° C. in a closed glass vessel in a microwave reactor for 25 minutes. The precipitate obtained after the 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 were obtained by literature methods (J. Org. Chem. 1995, 60, 4324).

Workup

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

Sources & evidence

ORD record
ord-9436f6743fcb40d1972ecff62ec8be16
Source dataset
uspto-grants-2013_12
Patent number
US08609731B2

Reaction notes

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