2-Bromonaphthalene → HCID 14272583, compound
Reaction equation
[Li]CCCC.Br[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1.[Sn:17](Cl)([CH2:26][CH2:27][CH2:28][CH3:29])([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH2:20][CH3:21]>>[CH2:26]([Sn:17]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:22][CH2:23][CH2:24][CH3:25])[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1)[CH2:27][CH2:28][CH3:29]Participants
4
Procedure
2.5 M of n-BuLi (1.9 mL/hexane, 4.83 mmol) was added to 2-bromonaphthalene (1 g, 4.83 mmol/THF (20 mL)) and reacted at −78° C. for 40 minutes under a dry and anaerobic operation condition to form a solution. SnBu3Cl (1.5 mL, 5.31 mmol) was then added to the solution and reacted at −78° C. for 1 hour. After returning to room temperature, the solution was continuously reacted for 8 hours. After the reaction was completed, the solution was extracted by ether (30 mL) and deionized water (50 mL). An organic phase was collected. After removal of ether by a rotary concentrator, the organic phase was purified by reduced-pressure distillation to form a transparent pale yellow oily product (22, 1.68 g, 83%).
Workup
- customreacted at −78° C. for 40 minutes under
- customa dry
- customanaerobic operation condition to form a solution
- customreacted at −78° C. for 1 hour
- customAfter returning to room temperature
- customthe solution was continuously reacted for 8 hours
- extractionthe solution was extracted by ether (30 mL) and deionized water (50 mL)
- customAn organic phase was collected
- customAfter removal of ether by a rotary concentrator
- distillationthe organic phase was purified by reduced-pressure distillation
- customto form a transparent pale yellow oily product (22, 1.68 g, 83%)
Sources & evidence
- ORD record
- ord-89f9e07f340b46bdb0c6a65568de6d1c
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08759543B2
Reaction notes
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