Carbon tetrabromide → HCID 67521426, compound

HRID 1925928Notes

Reaction equation

HRID 1925928 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[C:15]([CH2:16]O)=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[O:7]1)=[O:5])[CH3:2].C(Br)(Br)(Br)[Br:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[CH2:1]([O:3][C:4]([CH:6]1[C:15]([CH2:16][Br:19])=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[O:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 67521184HCID 67521184, compound

Product 1

HCID 67521426HCID 67521426, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To an ice-cooled mixture of 3-Hydroxymethyl-2H-chromene-2-carboxylic acid ethyl ester (1.73 g, 7.39 mmol) in methylene chloride (25 mL) was added commercially available carbon tetrabromide (2.70 g, 8.13 mmol) and commercially available triphenylphosphine (1.94 g, 7.39 mmol). After addition was complete the mixture was stirred at 0° C. for 6 hours. Upon completion of the reaction, the methylene chloride was removed under reduced pressure. The crude product obtained was purified by ISCO flash chromatography (Teledyne Isco RediSep Flash Column 40 g; (0% to 90% ethyl acetate/hexane) to afford 3-bromomethyl-2H-chromene-2-carboxylic acid ethyl ester as a yellow oil, 1.08 g (49% yield).

Workup

  1. additionAfter addition
  2. customUpon completion of the reaction
  3. customthe methylene chloride was removed under reduced pressure
  4. customThe crude product obtained
  5. customwas purified by ISCO flash chromatography (Teledyne Isco RediSep Flash Column 40 g

Sources & evidence

ORD record
ord-6ddd51ef30634c2c92c0d3f01675ecaf
Source dataset
uspto-grants-2012_05
Patent number
US08178689B2

Reaction notes

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