Carbon tetrabromide → Indole-bromide

HRID 966502Notes

Reaction equation

HRID 966502 reaction equation
C(OC([C:11]1[C:19]2[C:18]3CCC(CO)O[C:17]=3[CH:16]=[CH:15][C:14]=2[NH:13][C:12]=1C)=O)C1C=CC=CC=1.C(Br)(Br)(Br)[Br:28].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)Cl.CO>C(Cl)Cl>[Br-:28].[NH:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]=[CH:12]1

Participants

6

Reactant 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 21226129Dichloromethane methanolHCID 233938887-Hydroxymethyl-2-methyl-3,7,8,9-tetrahydro-pyrano[3,2-e]indole-1-carboxylic acid benzyl ester

Product 1

HCID 22381015Indole-bromideYield 83.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-Hydroxymethyl-2-methyl-3,7,8,9-tetrahydro-pyrano[3,2-e]indole-1-carboxylic acid benzyl ester (0.410 g, 1.16 mmol, 1 eq) was suspended in dry CH2Cl2 (20 mL) under Ar. Carbon tetrabromide (0.615 g, 1.86 mmol, 1.6 eq) was added followed by the addition of triphenylphosphine (0.441 g, 1.5 mmol, 1.3 eq). The reaction mixture was stirred at room temperature. The reaction was followed by TLC (CH2Cl2/MeOH 9/1). After 3 hours, the reaction mixture was loaded on silica gel and chromatographed, eluting with CH2Cl2/MeOH 9/1. 0.191 g (40% yield) of the indole-bromide was obtained as an unstable brown oil.

Workup

  1. customchromatographed
  2. washeluting with CH2Cl2/MeOH 9/1

Sources & evidence

ORD record
ord-6f299eebd8374fcb91b7b55d2ac5b058
Source dataset
uspto-grants-2005_10
Patent number
US06951848B2

Reaction notes

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