Carbon tetrabromide → HCID 12138347, compound

HRID 987174Notes

Reaction equation

HRID 987174 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([S:31][CH3:32])[CH:30]=1)[CH2:6][O:7][C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([O:16][CH2:17][C:18]2[CH:23]=[C:22]([S:24][CH3:25])[CH:21]=[C:20]([S:26][CH3:27])[CH:19]=2)[CH:15]=1)[CH2:11]O.C(Br)(Br)(Br)[Br:34].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:1][S:2][C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([S:31][CH3:32])[CH:30]=1)[CH2:6][O:7][C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([O:16][CH2:17][C:18]2[CH:23]=[C:22]([S:24][CH3:25])[CH:21]=[C:20]([S:26][CH3:27])[CH:19]=2)[CH:15]=1)[CH2:11][Br:34]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 12138346HCID 12138346, compound

Product 1

HCID 12138347HCID 12138347, compoundYield 286.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3,5-Bis-(3,5-dimethylthiobenzyloxy)benzyl alcohol (17.0 g, 0.033 mol) and carbon tetrabromide (14.2 g, 0.0043 mol) were dissolved in 100 ml of tetrahydrofuran. To this, triphenylphosphine (11.3 g, 0.043 mol) was added portionwise. at the temperature of 1.0 to 10° C. After completion of the addition, the mixture was stirred for 7 hours keeping the mixture at the same temperature. Then, the reaction mixture was poured into 300 ml of ice-water and the resulting mixture was extracted with chloroform. The extract was purified by means of chromatography, giving 7.0 g of 3,5-bis(3,5-dimethylthiobenzyloxy)benzyl bromide

Workup

  1. customat the temperature of 1.0 to 10° C
  2. additionAfter completion of the addition
  3. extractionthe resulting mixture was extracted with chloroform
  4. customThe extract was purified by means of chromatography

Sources & evidence

ORD record
ord-9e8fd6659aec4cdf9d3c90da6eb2251b
Source dataset
uspto-grants-2003_10
Patent number
US06630578B2

Reaction notes

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