Bromine → N-(4-Bromo-5,6,7,8-tetrahydronaphthalen-1-yl)-acetamide

HRID 751029Notes

Reaction equation

HRID 751029 reaction equation
[C:1]1([NH:11][C:12](=[O:14])[CH3:13])[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[Br:15]Br>CC(O)=O>[Br:15][C:4]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[C:1]([NH:11][C:12](=[O:14])[CH3:13])=[CH:2][CH:3]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 2320651-Acetamido-5,6,7,8-tetrahydronaphthalene

Product 1

HCID 12710300N-(4-Bromo-5,6,7,8-tetrahydronaphthalen-1-yl)-acetamideYield 91.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of compound 2A (2 g, 11 mmol) in AcOH (15 mL) cooled at 0° C. was added a solution of bromine (1.69 mL, 33 mmol) in AcOH (1.2 mL) slowly so that the reaction temperature was maintained below 17° C. After addition, the reaction mixture was stirred at rt until all the starting material was consumed (˜4 h). The reaction mixture was then poured into ice/water and the resulting suspension filtered. The collected solid was washed with H2O until the filtrate pH=6-7, and dried in a vacuum oven at 50° C. overnight to yield compound 2B (2.7 g) as an off-white solid.

Workup

  1. temperaturewas maintained below 17° C
  2. additionAfter addition
  3. customwas consumed (˜4 h)
  4. additionThe reaction mixture was then poured into ice/water
  5. filtrationthe resulting suspension filtered
  6. washThe collected solid was washed with H2O until the filtrate pH=6-7
  7. customdried in a vacuum oven at 50° C. overnight

Sources & evidence

ORD record
ord-35d67dc2579f4147a0e9b3b15ee29a97
Source dataset
uspto-grants-2008_07
Patent number
US07405234B2

Reaction notes

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