Carbon tetrabromide → HCID 117687689, compound

HRID 920871Notes

Reaction equation

HRID 920871 reaction equation
C(Br)(Br)(Br)[Br:2].[C:6]1([C:12]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21]O)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[C:6]1([C:12]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH:20]([Br:2])[CH3:21])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 11825346Ethanol, 2-[2-[2-(triphenylmethoxy)ethoxy]ethoxy]-

Product 1

HCID 117687689HCID 117687689, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of carbon tetrabromide (8.3 g, 25 mmol) and 10 g of 2-[2-(2-triphenylmethoxyethoxy)ethoxy]ethanol are stirred together in 75 mL dichloromethane at 0° C. To this solution is added a solution of 6.7 g triphenylphosphine (25 mmol) in 75 mL dichloromethane dropwise over 1½ hours at 0° C. After stirring for an additional 2 hours, the solution is evaporated to dryness and the residual solids are resuspended in 150 mL diethyl ether. The triphenylphosphine by-product is removed via vacuum filtration and the product is then purified via column chromatography over silica gel, eluting with dichloromethane.

Workup

  1. customthe solution is evaporated to dryness
  2. customThe triphenylphosphine by-product is removed via vacuum filtration
  3. customthe product is then purified via column chromatography over silica gel
  4. washeluting with dichloromethane

Sources & evidence

ORD record
ord-04bd209d2dc448ee814eb1632401324a
Source dataset
uspto-grants-2016_03
Patent number
US09273074B2

Reaction notes

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