Allyl bromide → HCID 81588513, compound

HRID 526662Notes

Reaction equation

HRID 526662 reaction equation
[Br:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][C:5]([OH:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[CH2:15](Br)[CH:16]=[CH2:17]>CN(C)C=O.CCCCCC.O.ClCCl.C(OCC)(=O)C>[Br:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][C:5]([O:10][CH2:17][CH:16]=[CH2:15])=[CH:4][CH:3]=1

Participants

9

Reactant 3

HCID 7841Allyl bromideHCID 19660Carbonate IonHCID 3871792-Bromo-5-hydroxybenzaldehyde

Product 1

HCID 81588513HCID 81588513, compound

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a dry 5 L three necked round bottom flask fitted with a condensor, temperature port, and stirrer, was added 6-bromo-meta hydroxyl benzaldehyde (2, 250 g, 1.23 moles) in dimethyl formamide (1250 mL). To the resulting solution was added anhydrous pottasium carbonate (538 g, 3.81 moles) under stirring. To this mixture was added slowly allyl bromide and reaction mixture maintained under stirring until the reaction was complete (monitored by thin layer chromatography (TLC) in hexane:dichlor-methane:ethyl acetate::7:4:0.5). After reaction completion dichloromethane and water were added and resulting solution stirred and layer separation carried out. The organic layer treated with 10% NaOH solution and layer separation repeated. The organic layer obtained was distilled out under reduced pressure to obtain 6-bromo-3-allyloxy benzaldehyde as a brownish liquid mass; yield 290 g (98%), purity by HPLC>95%. 1HNMR (CDCl3): 4.55-4.65 (s, 2H), 5.15-5.40 (m, 2H), 6.00-6.10 (m, 1H), 7.0-7.10 (dd, 1H), 7.18-7.24 (d, 1H), 7.52-7.56 (d, 1H), 10.1 (s, 1H, CHO)

Workup

  1. additionTo this mixture was added slowly
  2. temperaturemaintained
  3. stirringunder stirring until the reaction
  4. additionwere added
  5. customresulting solution
  6. stirringstirred
  7. customlayer separation
  8. additionThe organic layer treated with 10% NaOH solution and layer separation
  9. customThe organic layer obtained
  10. distillationwas distilled out under reduced pressure

Sources & evidence

ORD record
ord-09cf320e5f9a4817b095e7b122e76f85
Source dataset
uspto-grants-2016_05
Patent number
US09346738B2

Reaction notes

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