Dimethylformamide → 2-(3-Bromopropyl)-5-formyloxy-4,6,7-trimethyl-1,3-benzoxathiole

HRID 2308871Notes

Reaction equation

HRID 2308871 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.[OH:22][C:23]1[C:24]([CH3:38])=[C:25]([CH3:37])[C:26]2[O:30][CH:29]([CH2:31][CH2:32][CH2:33]O)[S:28][C:27]=2[C:35]=1[CH3:36].CN(C)[CH:41]=[O:42]>>[Br:20][CH2:33][CH2:32][CH2:31][CH:29]1[S:28][C:27]2[C:35]([CH3:36])=[C:23]([O:22][CH:41]=[O:42])[C:24]([CH3:38])=[C:25]([CH3:37])[C:26]=2[O:30]1

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 11776TriphenylphosphineHCID 24408BromineHCID 1275772-(3-Hydroxypropyl)-4,6,7-trimethyl-2H-1,3-benzoxathiol-5-ol

Product 1

HCID 148021802-(3-Bromopropyl)-5-formyloxy-4,6,7-trimethyl-1,3-benzoxathiole

Procedure

1.5 g of triphenylphosphine was dissolved in 3 ml of dimethylformamide, and then a solution of 0.9 of bromine in 2 ml of dimethylformamide was added dropwise. The mixture was allowed to react for 30 minutes at room temperature, after which 0.5 g of 3-(5-hydroxy-4,6,7-trimethyl-1,3-benzoxathiole-2-yl)propanol (prepared as described in Example 71) was added. The reaction mixture was allowed to react for a further 20 hours at room temperature. The same treatment and separation procedures as described in Example 75 were carried out. From the fraction eluted first was obtained 2-(3-bromopropyl)-5-formyloxy-4,6,7-trimethyl-1,3-benzoxathiole.

Workup

  1. customto react for 30 minutes at room temperature
  2. customto react for a further 20 hours at room temperature
  3. customThe same treatment and separation procedures
  4. washFrom the fraction eluted first

Sources & evidence

ORD record
ord-19a0119ff8914469b3cedddde0664844
Source dataset
uspto-grants-1987_09
Patent number
US04691027

Reaction notes

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